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Tuscany Cycling Guide

Introduction

Tuscany by bike is a  superb way to explore a region rich with castles, vineyards, olive groves, and medieval villages. Ride under the warm Tuscan sun and discover a visceral history that dates back to before the Roman Empire. Add in the wineries of Chianti and mouthwatering cuisine and you have a near-perfect cycling destination.

The following guide is a compilation of  background, safety and day-by-day routes of the area. Complete with restaurant suggestions and “Points of Interest,” this guide will provide you with thorough, applicable travel information for your next cycling tour through Tuscany.

The Day-by-Day section of the guidebook will preview each days route and scenery or points of interest along the way. It’s suggested that you read this before you head out on the day’s ride. Typically, there are three levels of riding each day: easiest, intermediate and challenge.

We are passionate about cycle touring and believe there is no better way to experience the sights, sounds and scents of an area than on two wheels.

Enjoy!
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Background on the Area

Highlights

Tuscany is located in central Italy and stretches from the Apennines to the Mediterranean. The landscape, food, wine, and history make this a bucket list destination for many. The quiet lanes and rolling hills make it a Mecca for cyclists.

The Etruscan, romans, and fiefdoms of the middle ages have all put their stamp on this area. A presence still visible today. Many of the towns of the area did not modernize and expand during the industrial revolution. These medieval time capsules, such as San Gimignano, have now been rediscovered and renovated. Tourism and agriculture are the major sources of income in the area in which you will be traveling.

Medieval villages, historic towns, castles and beautiful abbeys litter the countryside. Radda is one of the quieter hilltop towns – at the start of many people’s tours. Sant’Antimo, near Montalcino is a great example of an ancient abbey that you can visit on the Montalcino loop day.  Tuscany is also full of spas – ancient and modern. You can visit one of the older ones – Bagno Vignoni – when riding from Montalcino to Montepulciano.

Our tours focus on some of the most scenic and historically interesting parts of Tuscany: specifically the areas of Chianti, Val d’Elsa, Val di Merse, The Crete Senesi, Val d’Orcia and Amiata.

Chianti is above all a wine region – not an administrative region – and includes parts of the Tuscan provinces of Florence, Siena, Arezzo and Pisa. In addition to the red wine, many producers make the dessert wine Vin Santo as well as olive oil.

The Elsa that formed the Val d’Elsa is 63 km long and rises in the municipality of Sovicille then flows into the Arno just west of Florence. The area combines industrial centers such as Piggiobonsi as well as architectural gems such as San Gimignano. Certaldo and Colle di Val d’Elsa get less tourist but are also worth a visit.

The fertile Val di Merse is southwest of Siena. The terrain is a mix of open farmland and – further south – dense forests and streams, including the River Merse itself. The most famous architectural site is the ruined Abbazia di San Galgano. The village of Sovicille is also surrounded by ancient castles, bridges and monasteries.

The Crete Senesi refers to an area of the Italian region of Tuscany to the south of Siena. Crete senesi are literally “Senese clays.” This gray clay, known as mattaione, represents the sediments of the Pliocene sea which covered the area between 2.5 and 4.5 million years ago. The most noteworthy site in the area is the monastery of Monte Oliveto Maggiore. The region is also known for its production of white truffles.

The Val d’Orcia extends from the hills south of Siena to Monte Amiata. It is characterized by gentle, carefully cultivated hills occasionally broken by rough gullies. It includes picturesque towns and villages such as Pienza (rebuilt as an “ideal town” in the 15th century under the patronage of Pope Pius II), Radicofani (home to the notorious brigand-hero Ghino di Tacco) and Montalcino (the Brunello di Montalcino is counted among the most prestigious of Italian wines). It is a landscape has become famous through its depiction Renaissance paintings and modern photography alike. In 2004, the Val d’Orcia was added to the UNESCO list of World Heritage Sites.

Monte Amiata (La Vetta) is a large lava dome and the highest point in southern Tuscany. The last major eruption was 300,000 years ago. The lower slopes of Amiata are peppered with small, pretty, villages and there are ski areas on the upper slopes. The main economic resources of the Amiata region are chestnuts, timber and, increasingly, tourism.

Climate

The best months to visit Tuscany are May through October, when the temperatures are pleasantly warm and the risk of rainfall lower. In summer, temperatures are never stifling and there is often a pleasant breeze. Spring and fall are great times to ride but the risk of rain rises as you get into October. We do not recommend cycling here in winter.

The charts below show the monthly average temperatures (in Fahrenheit) and rainfall (in inches) for Siena. The temperatures in the higher hilltop towns, such as Montepulciano, tend to be a few degrees cooler.

Average Monthly Temperatures in Fahrenheit
Average Monthly Rainfall in Inches

A Little History

Tuscany is named after its pre-Roman inhabitants, the Etruscans. It was ruled by Rome for many centuries. In the Middle Ages, it saw many invasions, but in the Renaissance period it helped lead Europe back to “civilization”. Later, it settled down as a grand duchy. It was conquered by Napoleonic France in the late 18th century and became part of the Italian Republic in the 19th century.

Pre-Etruscan

The pre-Etruscan history of the area in the late Bronze and Iron Ages parallels that of the early Greeks. The Tuscan area was inhabited by peoples of the Apennine culture in the late second millennium BCE (roughly 1350–1150 BCE) who had trading relationships with the Minoan and Mycenaean civilizations in the Aegean Sea. Following this, the Villanovan culture (1100–700 BCE) saw Tuscany taken over by chiefdoms. City-states developed in the late Villanovan period (paralleling Greece and the Aegean) before “Orientalization” occurred and the Etruscan civilization rose.

Etruscan Period

The Etruscans were the first major civilization in this region; large enough to lay down a transport infrastructure, implement agriculture and mining, and produce vivid art. They reached their peak during the 7th century BCE and 6th century BCE, finally succumbing to the Romans by the first century. One reason for their eventual demise was the increasing absorption of surrounding cultures, including the adoption of the Etruscan upper class by the Romans.

Roman

Soon after absorbing Etruria, Rome established the cities of Lucca, Pisa, Siena, and Florence. These developments included extensions of existing roads, introduction of aqueducts and sewers, and the construction of many buildings, both public and private. The Roman civilization in the West collapsed in the fifth century and the region was left to the Goths, and others. In the sixth century, the Longobards arrived and designated Lucca the capital of their Duchy of Tuscia.

Middle Ages

After the fall of the Western Roman Empire the region fell under Ostrogoth and Byzantine control, before the Lombard conquest in 569. After the destruction of the Lombard kingdom by Charlemagne, it became a county first, and then a march. In the 11th century the marquisate went to the Attoni family from Canossa, who also held Modena, Reggio Emilia and Mantua. Matilda of Canossa was their most famous member.

In this period Tuscany acquired many castles, abbeys and monasteries, while the main towns grew, turning themselves into communes mostly independent from the Holy Roman Empire.

Pilgrims travelling along the Via Francigena between Rome and France brought wealth and development during the Middle Ages. The food and shelter required by these travelers fuelled the growth of communities around churches and taverns.

In the 11th century Pisa became the most powerful Tuscan city but began to decline in the 14th century after its defeat by Genoa at the Battle of Meloria. Florence then gained the ascendancy with its conquest of Arezzo and Pisa in the early 15th century and become the cultural capital of the region. Florence then declares itself a republic. Florence’s only remaining rival in Tuscany was Siena.

Renaissance Period

From the 1430s, Florence was dominated by the increasingly monarchical Medici family weakening the principles of the republic. For much of the time, the Medici ruled without a title or formal office. They also presided over the Florentine Renaissance.

There was a return to the republic from 1494 to 1512 when Cardinal Giovanni de’ Medici retook the city with Spanish forces before going to Rome to become Pope Leo X. Florence was then dominated by a series of papal proxies until 1527 when the citizens again declared it a republic … only to have it taken from them again in 1530 after a siege by the Spanish army. At this point Pope Clement VII and Charles V appointed Alessandro de’ Medici as the first formally hereditary ruler.

The Sienese commune was not incorporated into Tuscany until 1555, and during the 15th century Siena enjoyed a cultural ‘Sienese Renaissance’ with its own more conservative character. Lucca also remained an independent Republic until 1847 when it became part of Grand Duchy of Tuscany in a popular plebiscite.

Grand Duchy of Tuscany

The Grand Duchy of Tuscany (Granducato di Toscana) was a central Italian monarchy that existed, with interruptions, from 1569 to 1859, replacing the Duchy of Florence but with its capital still in Florence. Tuscany was then ruled by the House of Medici until 1737. The grand duchy thrived under these Medici and enjoyed economic and military success.

After the Medici dynasty died out, there was a take-over by Habsburg-Lorraine rulers. Francis Stephen of Lorraine (a distant relation of the Medici) succeeded the family and ascended the Tuscan throne – however, Tuscany was governed by a viceroy for his entire rule. His descendants then ruled, and resided in, the grand duchy until 1859, barring one interruption, when Napoleon Bonaparte gave Tuscany to the House of Bourbon-Parma.

Following the collapse of the Napoleonic system in 1814, the grand duchy was restored. The United Provinces of Central Italy, a client state of the Kingdom of Sardinia-Piedmont, annexed Tuscany in 1859. Tuscany was then formally then annexed to Sardinia in 1860, following a landslide referendum, in which 95% of voters approved.

Italian Republic

In 1860 Tuscany became part of modern Italy. Florence replaced Turin as Italy’s capital in 1865, hosting the country’s first parliament, and was superseded by Rome six years later, in 1871.

Vineyards & Wines

Introduction

There are over 1000 vineyards in the Tuscany – but then every small farm seems to grow their own grapes! Tuscany has 42 DOCs and 11 DOCGs.

DOCs (Denominazione di Origine Controllata) wines are the more common though as the rules governing quality and authenticity are less strict than those for DOCG status. For example, the geographic zone might be a little bigger or the rules about the variety of grapes used might be a little more relaxed.

DOCGs (Denominazione di Origine Controllata e Garantita) are for wines produced to stricter regulations. The wine is regularly tested by a committee that then guarantees the geographic authenticity of the wine and its quality. There are currently only a handful of Italian wines that qualify for DOCG status.

Tuscany DOCGs that you will almost certainly see during your trip include:

  • Brunello di Montalcino,
  • Chianti Classico,
  • Vernaccia di San Gimignano,
  • Vino Nobile di Montepulciano.

The Local Wines to Look For

Brunello

Brunello di Montalcino is a red Italian wine produced in the vineyards surrounding the town of Montalcino. Brunello, a diminutive of Bruno, a male name which means brown. It was given locally to what was believed to be an individual grape variety grown in Montalcino. In 1879 it was determined that Sangiovese and Brunello were, in fact, the same grape variety. In Montalcino the name Brunello evolved into the designation of the wine produced with 100% Sangiovese grapes.

The modern version of Brunello was “invented” in the late-19th century by a local farmer named Ferruccio Biondi-Santi who released the first “modern” version of Brunello di Montalcino that was aged for over a decade in large wood barrels. The family winery – Biondi Santi – is still going strong and can easily be reached from Montalcino.

Brunello is a strong full bodied complex dry red wine and is a very good wine to age. Some wineries claim that their wines can age over 100 years. The flavors that can be sensed are those of cherries, plums, vanilla, wood, tobacco, herbs and caramel. A young Brunello is complex and heavy on the tannins, when aged the tannins decrease and the wine becomes softer.

In 1980, Brunello di Montalcino was awarded the first Denominazione di Origine Controllata e Garantita (DOCG) designation and today is one of Italy’s best-known and most expensive wines. The number of producers of the wine has grown from only 11 in the 1960s to more than 200 today, producing some 330,000 cases of the Brunello wine annually.

Chianti

The history of Chianti dates back to at least the 13th century. The earliest incarnations of Chianti were as a white wine.

In the Middle Ages, the villages of Gaiole, Castellina and Radda located near Florence formed a Lega del Chianti (League of Chianti) creating an area that would become the spiritual and historical “heart” of the Chianti region and today is located within the Chianti Classico Denominazione di Origine Controllata e Garantita (DOCG).

As the wines of Chianti grew in popularity other villages in Tuscany wanted their lands to be called Chianti. The boundaries of the region have seen many expansions and sub-divisions over the centuries.

In addition to changing boundaries, the grape composition for Chianti has changed dramatically over the years. The earliest examples of Chianti were a white wine but gradually evolved into a red. Baron Bettino Ricasoli, the future Prime Minister in the Kingdom of Italy created the first known “Chianti recipe” in 1872, recommending 70% Sangiovese, 15% Canaiolo and 15% Malvasia bianca.

In 1967, the Denominazione di origine controllata (DOC) regulation set by the Italian government firmly established the “Ricasoli formula” as the standard.

The variable terroir of these different macroclimates contributed to diverging range of quality on the market and by the late 20th century consumer perception of Chianti was often associated with basic mass-market Chianti sold in a squat bottle enclosed in a straw basket, called fiasco. However, in the last few years quality has greatly improved and, today, Chianti Classico is a well-respected wine which has earned its place amongst the great wines of Italy – even more so for Chianti Classico Riserva, which needs to age for 24 months with a minimum of 3 months in bottle and 21 in wood.

Young Chianti wines have a fresh fruity somewhat sharp drink while older Riserva wines become more full bodied and soft. A Chianti Classico Riserva can age for quite a bit longer than a normal Classico, but the aging process can remove part of the fruity taste when the bottle is kept too long.

Vernaccia di San Gimignano

Vernaccia is a white wine made from the Vernaccia grape, produced in and around San Gimignano. Since the Renaissance it has been considered one of Italy’s finest white wines. It was the first Italian wine to be awarded Denominazione di Origine Controllata (DOC) status in 1966. In 1993 it was upgraded to Denominazione di Origine Controllata e Garantita (DOCG) status.

The earliest recorded mention of the wine is in 1276. Due to the difficulties in cultivating the Vernaccia grape, the wine fell out of favor in the early 20th century as the more prolific Trebbiano and Malvasia grapes were planted. By the 1960s, Vernaccia di San Gimignano experienced a resurgence as its distinctive, crisp qualities established it as a popular alternative to the blander wines produced from Trebbiano and Malvasia blends.

The wine is characteristically dry with crisp acidity and a slightly bitter finish. Most consider Vernaccia di San Gimignano to be a simple, everyday white. Modern winemaking has introduced the use of oak aging to give the wine another layer of complexity and roundness making modern Vernaccia di San Gimignano very different from the historic Vernaccia.

According to DOC regulations, Vernaccia di San Gimigniano must contain 90% Vernaccia, with up to 10% other nonaromatic approved white varieties. In order to meet “riserva” status. Aging must be for a minimum of twelve months, including four months in bottle.

Vino Nobile di Montepulciano

Vino Nobile di Montepulciano is a red wine produced in the vineyards surrounding the town of Montepulciano. In the medieval ages Nobile di Montepulciano was known as one of the best wines in Italy but in more recent times lost that reputation to the other great wines such as Brunello, Barolo and Amarone.

The color is bright ruby red but turns more towards garnet when it ages. Nobile di Montepulciano is a rounded satin-like dry red wine. Flavors that can be identified within this wine are those of cherries, forest fruit, violets, vanilla and wood.

The wine is made primarily from the Sangiovese grape varietal (known locally as Prugnolo gentile) (minimum 70%), blended with Canaiolo Nero (10%–20%) and small amounts of other local varieties such as Mammolo. The wine is aged in oak barrels for 2 years; three years if it is a riserva. Nobile di Montepulciano can be kept between about 10 and 15 years and is ready for consumption starting at 3 years old.

Recently this wine has been regaining ground thanks to the efforts of local wineries that have increased the quality of the wine while still keeping the price reasonable.

In 1966 the wine was claasified as DOC (Denominazione di Origine Controllata) and DOCG (Denominazione di Origine Controllata e Garantita) was authorized by in 1980.

Did you Know?

Did you know that from one acre of vineyards one can harvest 5 tons of grapes, 13½ barrels of wine, 4,000 bottles of wine or 16,000 glasses of wine?

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Towns and Cities

Asciano

Overview

Asciano has ancient roots having been an Etruscan, Roman and Lombard settlement. Now, however, it is a Ascianosleepy town partly surrounded by 13th-century walls. Asciano is far enough off the main tourist routes to avoid the mass tourism of the tour buses but interesting enough to attract more independent explorers. As such, it is pleasantly and welcoming with a good range of facilities.

Most of the town’s sites, stores and restaurants are clustered along the main street through the old town: Corso Giacomo Matteotti. Halfway along this road, the small central square (Piazza Giuseppe Garibaldi) is a nice place to sit and watch the town go about its business. The square also has a bakery, a small store and a café.

In terms of sights, the town boasts a museum with a surprisingly good collection of Sienese art as well as a Romanesque basilica. RespectivelyMuseo D’Arte Sacra and Basilica di Sant’Agata.

AscianoThe Museum of Sacred Art is housed in the nicely restored Palazzo Corboli at the northern end of Corso Giacomo Matteotti. It includes Etruscan relics, works by Sienese artists from the 14th to the 16th centuries, and wooden sculptures by Giovanni Pisano and Francesco di Valdambrino.

The Romanesque basilica of Sant’Agata is at the southern end of Corso Giacomo Matteotti. The church was founded in the 11th Century and built of travertine. The nave was then restored in the 12th Century. However you look at it, it’s pretty old! Inside the church are two notable 16th-century frescoes, one by Il Sodoma and one attributed to Bartolomeo Neroni.

Eating & Drinking

Where you eat dinner will depend largely on where you are staying. If you are staying at Borgo Casabianca, you will, most likely, eat there. If you are staying at Podere Alberese, the owners will take you to the local taverna or to Borgo Casabianca.

If you are staying in Asciano or eating lunch in Asciano, you have a wider selection including the following.

Probably the best food in town is served at Locanda Amordivino. Nice ambiance and a pleasant outdoor terrace at the back of the restaurant. They serve well-prepared Tuscan food with a specialty of grilled meats. Service can be a little slow and prices are relatively high for a small town though nothing like Florence or Siena. Open: 12.30PM – 2.15PM Wednesday to Monday. Closed on Tuesdays. Address: At the northern end of the main street at Corso Giacomo Matteotti, 128, 53041 Asciano. +39 577 165 6607.

For a more casual, less expensive lunch – and the option of pizza – head to the family-run Ristorante La Mencia. There is also a shady garden in the back. Service here can be slow too. Open: 12:15PM – 2:30PM Ristorante_La_MenciaTuesday to Sunday. Closed on Mondays. Address: Halfway along main street at Corso Giacomo Matteotti, 85, 53041 Asciano. +39 0577 718 227. https://www.lamencia.it/en/index.html

Another solid choice is L’Angolo dello Sfizio. Open: 12:00PM – 3:00PM Tuesday to Sunday. Closed on Mondays. Address: Also on the main street at Corso Giacomo Matteotti, 35, 53041 Asciano. +39 0577 717128.

For an alternative to a formal sit-down lunch, the bakery of Panificio Il Forno delle Crete serves pizza by the slice and nice baked goods. Open from 7:00AM Monday to Saturday. Closed on Sundays. Address: Located on the cetral square at Piazza Giuseppe Garibaldi, 5, 53041 Asciano. +39 577 718 558. https://www.ilfornodellecrete.com/en/home

There is also a nice café/bar next-door to the bakery and a small supermarket on the opposite side of the square.

Sites and Things to Do

Sites

Museo D’Arte Sacra (Museum of Sacred Art) at Corso Giacomo Matteotti, 122, 53041 Asciano. +39 0577 714450. Open Sunday and Monday from 10:30AM to 1:00PM and 2:00PM to 5:00PM, and Wednesday and Saturday from 2:00PM – 5:00PM. Closed Tuesdays, Thursdays, and Fridays. https://museo-palazzo-corboli.business.site/

Basilica di Sant’Agata is open daily from 9:00AM to 7:00PM. Address: the northern end of Corso Giacomo Matteotti / Piazza della Basilica, 10, 53041 Asciano.

Useful Contacts

Tourist Information Office: The tourist office is located in the Palazzo Corboli with the Sacred Art Museum at Corso Giacomo Matteotti, 122. Follow signs to “i informazione”. Staff at Italian tourist offices typically speak good English and are a great source of local knowledge and town maps. +39 0577 719 510.

AlimentariStores: There is a small supermarket (Alimentari) on the central piazza (Piazza Giuseppe Garibaldi). Just north of the square is the more interesting Natura e Delizie store with the basics as well as organic fruit and vegetables – located at Corso Giacomo Matteotti, 46. There is also a large Coop supermarket on the way out of town at Via Grottoli, 30. All these stores close for lunch, typically between 1:00PM – 4:00PM.

A Little History

Asciano has its origins as Etruscan, Roman and Lombardy settlements. A 5th century BC Etruscan necropolis has been excavated nearby and remains of Roman baths, with a fine mosaic pavement, were found within the town in 1898.

During the medieval period its location made it a site of contest between Siena and Florence: the Battle of Montaperti was fought nearby on 4 September 1260. The village was then purchased by the Sienese in 1285 and surrounded by walls in 1351.Asciano

The village was controlled by Siena until 1554 when Asciano became part of the holdings of the Medici Grand Duchy (of Florence) and from then gained a growing economic importance thanks to the development agriculture (cereals, oil and wine) and industry (artisan working of leather and ceramics).

Domination by the Medicis lasted until the beginning of the 18th century when the last descendent of the de’Medici family was succeeded by the Dukes di Lorena. In 1861, Asciano was annexed to the Kingdom of Italy by King Vittorio Emanuele II of Savoia.

Montalcino

Overview

After climbing for ten kilometers, you will not need telling that Montalcino is a hilltop town. The town is a perfect example of a fortified hilltop city; encircled by fortified walls, protected by a medieval castle and little changed in appearance since the 16th century. From many vantage points you get outstanding views of the Montalcinosurrounding countryside: rolling hills, ancient oak trees, olive groves, and, of course, the vineyards that produce the famous Brunello wine.

Much of the town’s wealth comes from the production and marketing of Brunello; one of the most renowned and appreciated Italian wines. Montalcino was already well-known for its fine red wines during the 15th century. However, the formula for Brunello was invented in 1888 by Ferruccio Biondi Santi, who had the idea of leaving out the grapes used in the traditional Chianti recipe, such as Canaiolo and Colorino, and using only the Sangiovese variety. Once produced, Brunello must be age for a minimum of 5 years, 2 of which must take place in oak barrels.

MontalcinoBut Montalcino is not just about wine. The historic center is dominated by the mighty and imposing Rocca (fortress). The views from its ramparts are spectacular, stretching towards Monte Amiata, across the Crete to Siena, and across the Val d’Orcia and the hills of the Maremma.

Another landmark of Montalcino is the tall and slender clock tower that graces the Palazzo dei Priori, the city’s town hall, while below lies the main square known as Piazza del Popolo with its characteristic Gothic loggia (a room with one or more open sides). The Palazzo Vescovile and the churches of Sant’Agostino, Sant’Egidio and San Francesco are also worth a look. But perhaps most enjoyable is to simply meander the lanes and alleyways pausing in cafes, craft shops and, of course, wine bars along the way.

Eating & Drinking

Where you eat will depend largely on where you are staying. If you are staying at Castello di Velona you will most likely eat there as it is several kilometers outside of Montalcino.

If you are staying at Canalicchio di Sopra please note the hotel is outside of town with no restaurant. For dinner, we can arrange a transfer to a local restaurant (usually €25 each way) or you can walk into Montalcino (1 mile along a dirt track) and take a taxi back. Just let us know which option you would prefer when you book.

If staying at the SI Montalcino Hotel, you may choose to eat at the hotel restaurant or walk into town.

In Montalcino, despite it being a popular tourist destination, there are several good places to eat.

Re di Macchia is one of the best restaurants in town – with meticulously prepared, traditional Tuscan food andMontalcino attentive service. It is located quite close to the Il Giglio Hotel at Via Soccorso Saloni, 21, 53024 Montalcino. Open: 12:00PM – 2:00PM from Friday to Wednesday. Closed on Thursdays +39 0577 846116. Reservations for dinner recommended.

You are less likely to need a reservation at Taverna del Grappolo Blu. The food is not quite as good as Re di Macchia and is a little less traditional in its preparation but it is still a good choice. A little closer into the center of town on a very small lane between Via delle Scuole and Via Giuseppe Mazzini at Scale di Via Moglio, 1. Open from 12:00PM – 3:00PM, and 7:00PM – 1-:00PM every day. +39 0577 847150. http://www.grappoloblu.it/

If you are staying at Il Giglio, the hotel has a nice restaurant: Il Giglio at Via Soccorso Saloni, 5. +39 0577 848 167. https://www.gigliohotel.com/?lang=en

Sites and Things to Do

Sites

the_RoccaAt the entrance to the town – near where our rides start and end – is the Rocca. This fortress has remained practically intact since the Middle Ages. There are outstanding views from the ramparts. Open: 9:00AM to 7.30PM Tuesday to Sunday. Closed on Mondays. Piazzale della Fortezza 1. +39 0577 846 014. Admission €5.

Another landmark of Montalcino is the slender clock tower that graces the Palazzo dei Priori, the city’s town hall. Open: 9:00AM – 5:30PM Monday to Saturday. Closed on Sundays. Address: Costa del Municipio, 2.

Museo Civico e Diocesano, has a good collection of religious paintings and sculptures. Open: 10.00AM – 1:00PM and 2:00PM – 6:00PM. Closed on Mondays. Address: Via Ricasoli, 31. + 39 0577 846 014. Admission €6.00.

Wine Tasting

There is no shortage of places to drink Brunello in town. One of the best is Enoteca di Piazza Montalcino. With over 100 wines to choose from this is a great way to taste a range of Brunellos (and other wines such as Rosso di Montalcino, Nobile di Montepulciano, and Chianti Classico) without scouring the countryside. The staff is knowledgeable and friendly. They can also arrange shipping back to US. They have some seating out on the street but the real thing happens in the cool wine room. Open: 9:00AM – 7:00PM every day. Located close to the center of town, address: Piazza Giuseppe Garibaldi, 4, 53024 Montalcino. +39 0577 849 194. https://www.enotecadipiazza.com/

If you want to visit a winery but do not want to ride, you can walk to Il Palazzone from the center of town. The winery is run by husband and wife team Laura and Marco, who will help you both “taste and understand” Brunello. Their motto is, “We drink what we can and sell the rest.” From the end of the ride, take the 3rd exit onIl_Palazzone the roundabout (staying on SP 14) then immediately take a right turn on Via del Poggiolo; after the pharmacy. The winery is about 300 meters down this lane that turns to dirt after passing the cemetery on LHS. Address: Località le Due Porte, 245, 53024 Montalcino. +39 0577 846142. Open Mon to Fri but given the distance, it might be worth calling ahead if you plan to visit. http://www.ilpalazzone.com/en

Just a short ride from Montalcino is NostraVita Winery. NostraVita, meaning ‘Our Life’ is a family run venture in a stunning location. The grapes are organically grown and certified, and the wine is made in cellars a stone’s throw away from the house. They do a full tour and tasting that lasts between an hour and a half and it is complimentary. You have the opportunity to purchase their wine after your tour. Reservations are essential. Address: Località Nostra Signora della Vita, 53024 Montalcino (SI). +39 329 442 3163. http://www.nostravita.it/

Useful Contacts

Tourist Information Office: Costa del Municipio, 1. +39 0577 849 331. Follow signs to “i informazione”. Staff at Italian tourist offices typically speak good English and are a great source of local knowledge and town maps.

Stores: Plenty of small stores in the historic old town. For a larger range, there is a Coop – also in the old town – at Vicolo Sant’Antonio, 7. Entrance at the corner of Via Sant’Agostino and Viale della Libertà. Open 8:30 AM to 1:00 PM and 4:00 PM to 7:30 PM. + 39 0577 847079.

A Little History

Like most of the towns you stay in on this tour, the place now occupied by Montalcino has been settled since Etruscan times. There was also a church here in the 9th century, most likely built by monks associated with the nearby Abbey of Sant’Antimo. The town takes its name from a variety of oak tree that once covered the terrain.

MontalcinoThe population grew suddenly in the middle of the tenth century, when people fleeing the nearby town of Roselle took up residence in the town. (In 935 the town of Roselle was destroyed by Saracens.)

During medieval times the city was known for its tanneries and for the shoes and other leather goods that were made from the high-quality leathers that were produced there.

During the late Middle Ages it was an independent commune with considerable importance owing to its location on the Via Francigena (see box in the San Gimignano section below), the main road between France and Rome, but increasingly Montalcino came under the sway of the larger and more aggressive city of Siena.

As a satellite of Siena since the Battle of Montaperti in 1260, Montalcino was heavily impacted by the conflicts in which Siena became embroiled; most notably those with Florence in the 14th and 15th centuries. Also, like many other cities in central and northern Italy, the town was caught up in the internecine wars between the Ghibellines (supporters of the Holy Roman Empire) and the Guelphs (supporters of the Papacy). Factions from each side controlled the town at various times in the late medieval period.

Once Siena had been conquered by Florence under the rule of the Medici family in 1555, Montalcino held out for almost four years, but ultimately fell to the Florentines, under whose control it remained until the Grand Duchy of Tuscany was amalgamated into a united Italy in 1861.

Gradual economic decline has recently been reversed by economic growth due to the increasing popularity of the town’s famous wine: Brunello di Montalcino. The number of producers of the wine has grown from only 11 in the 1960s to more than 200 today, producing some 330,000 cases of the Brunello wine annually.

Montepulciano

Overview

MontepulcianoMontepulciano is attractive from both afar (a cluster of red-brick buildings perched on a hilltop) and from within, where the main street runs almost a mile along a narrow ridge. The topology of the town provides outstanding views of the surrounding countryside down alleyways and from the back windows of its many cafés and restaurants. The town is relatively high for the area, sitting at 605 meters giving it pleasantly cooler summer evenings.

Montepulciano is a major producer of food: pork, cheese, “pici” pasta, lentils, and honey. It also produces a world renowned wine in Vino Nobile di Montepulciano as well as the not-quite-so-famous Rosso di Montepulciano.

The main street of Montepulciano stretches for over one kilometers from Porta al Prato to the Piazza Grande at the top of the hill. The street is generally known as the Corso but changes its formal name from Via di MontepulcianoGracciano Nel Corso, through Via di Voltaia Nel Corso to Via dell’Opio Nel Corso. At the end of the Corso take a sharp right onto Via del Teatro to get to the Piazza Grande. It is worth the walk – both to enjoy strolling along the Corso with its shops, cafes and restaurants and also for the destination of the Piazza Grande with its impressive palaces and cathedral. In fact the mostly car-free streets and lanes are great for wandering in – and getting lost in. But you can’t get very lost as the 14th-century city walls are never far away – with their expansive views.

City landmarks include:

  • The Palazzo Comunale, designed by Michelozzo in the tradition of the Palazzo della Signoria (Palazzo Vecchio) of Florence.
  • Palazzo Tarugi, attributed to Antonio da Sangallo the Elder or Jacopo Barozzi da Vignola. It is entirely in travertine, with a portico which was once open to the public.
  • The Cathedral of Santa Maria Assunta, (Duomo di Montepulciano), constructed between 1594 and 1680, includes a masterpiece from the Sienese School, a massive Assumption of the Virgin triptych painted by Taddeo di Bartolo in 1401.

Just outside of the city, the large dome pf the Sanctuary of the Madonna di San Biagio helps give the city its distinctive profile – when approached from the south or west. It was designed by Antonio da Sangallo the Elder and built between 1518 and 1545.

Eating & Drinking

In the town of Montepulciano:

Probably the best restaurant in town is Le Logge del Vignola – though not the cheapest! They just seem to get everything right: food, service and wine. It is also conveniently located in the old town, just off the Corso at Via delle Erbe 6. Open: 12:30PM – 2:30PM and 7:30PM – 10:30PM Wednesday to Monday. Closed Tuesdays. +39 0578 717 290. Reservations recommended. http://www.leloggedelvignola.com/en/

Ristorante_La_GrottaAnother top eatery is Ristorante La Grotta – located in a 16th-century building just outside of the city walls across from St. Blaise’s Church. They also have a nice garden in which they serve dinner in the summer. It is about a one kilometer walk from the Piazza Grande, address: Via di S. Biagio, 15, 53045 Montepulciano. Open: 12:30PM – 2:15PM and 7:30PM – 10:00PM Thursday to Tuesday. Closed Wednesdays. +39 0578 757 479.  Reservations recommended. http://www.lagrottamontepulciano.it/intro.php

At the less formal end of the spectrum – but still with great food and lots of atmosphere – is Osteria Acquacheta. The food is excellent but you need to be OK with cosy, communal seating at a few long tables. The proprietor, Guilio, also has some quirky “rules” such as only getting one glass for both water and wine. A real experience! Fills up so worth being a little early. Open: 12:30PM – 3:00PM and 7:30PM – 10:30PM from Thursday to Monday. Closed Tuesday and Wednesday. Address: Just down from Piazza Grande at Via del Teatro, 22, 53045 Montepulciano. +39 0578 717 086. https://www.acquacheta.eu/

Trattoria di Cagnano is another nice, mid-level restaurant with probably the best pizza in Montepulciano – as well as more traditional dishes. Conveniently located on the Corso at Via dell’Opio Nel Corso, 30. Open: 12:30PM – 2:30PM and 7:30PM – 10:00PM from Tuesday to Sunday. Closed Mondays. +39 0578 758 757. https://www.trattoriadicagnano.it/

If you are staying at Villa Cicolina, you will most likely eat at their restaurant, which is one of the best in the area.

If you are staying at Villa Poggiano, you will need to take a taxi into town for dinner. We suggest you ask the hotel to arrange this on your arrival (typically €25 one way). The exception is if you have taken the hotels cooking class (at 4:00PM by prior arrangement), in which case you enjoy what you have cooked for dinner.

Sites and Things to Do

Sites in the Piazza Grande

The Palazzo Comunale. Open 10.00AM – 1.00PM and 2.00PM – 6.00PM. Admission €5.00. Address: Piazza Grande, 1, 53045 Montepulciano. +39 0578 7121

Palazzo Tarugi – is an impressive monument not open to the public but beautiful from the outside!

The Cathedral of Santa Maria Assunta, (Duomo di Montepulciano) is open daily from 9:00AM – 1:00PM and 3:30PM – 7:00PM. Admission free. Address: Piazza Grande, 53045 Montepulciano. +39 0578 71951.

 Other Sites

Sanctuary of the Madonna di San Biagio (Chiesa di San Biagio) is just outside the city walls at the end of Viale della Rimembranza. Open 10:00AM – 6:00PM. +39 0578 757290. https://www.tempiosanbiagio.it/

Useful Contacts

Tourist Information Office: In the Porta al Prato parking lot, just outside of the city walls at Minzoni G. (Piazza). + 39 0578 757 341 Open 9:00AM – 1:00PM and 3:00PM – 7:00PM. Closed Sunday PM. Follow signs to “i informazione”. Staff at Italian tourist offices typically speak good English and are a great source of local knowledge and town maps.

Stores: Plenty of small stores in the historic old town. For a larger range, there is a Conad supermarket, outside of the city walls, down the hill on RHS heading north on SP 17 at Via Elio Bernabei, 4. +39 0578 716 731. Open 8:30AM – 8:00PM.

A Little History

According to legend, Montepulciano was founded by the Etruscan King Lars Porsena of Chiusi. In Roman times it was the seat of a garrison guarding the main roads of the area.Montepulciano

After the fall of the Western Roman Empire, the town developed as a religious center under the Lombards. In the 12th century it was repeatedly attacked by the Republic of Siena, which the people of Montepulciano (also known as Poliziani) faced with the help of Perugia, Orvieto, and, sometimes, Florence. The 14th century was characterized by constant struggles between the local noble families, until the Del Pecora family became rulers of the town.

From 1390, Montepulciano was a loyal ally (and later possession) of Florence and, until the mid-16th century, enjoyed a period of splendor with architects such as Antonio da Sangallo the Elder, Jacopo Barozzi da Vignola, and Baldassarre Peruzzi building luxurious palaces.

In 1559, when Siena was conquered by Florence, Montepulciano lost its strategic role as a defensive outpost and its importance declined.

After the unification of Italy and the drying of the Val di Chiana, the town became an important agricultural center while its industrial activities tended to move to Chiusi, which was nearer to the railroad being built in that period.

Radda

Overview

The beauty of Radda in Chianti is that the old town is small, pedestrianized and seems little-changed since Raddamedieval times. It has enough tourism to justify its restoration and preservation but not so much as to overwhelm its character. The historic old town is enclosed within medieval walls and consists of little more than one “main” road (Via Roma), a small central square and a handful of small arterial alleyways.

There are no outstanding sites – the main attraction is the ambiance and the setting – though the covered 14th-century walkway that circles part of the city is worth a visit.

Eating & Drinking

If you are staying in Radda:

One of the best places for fine dining (but not overly formal) in Radda is La Botte di Bacco. Tuscan cooking but prepared with a lightness and originality that makes this restaurant stand out. The chef/owner and his wife provide excellent and very personal service. The only negative is that some wines are a little higher-priced than typical for restaurants in the area. Open: 12:00PM – 2:30PM and 7:00PM – 9:00PM from Friday to Wednesday. Closed on Thursdays. Address: Via XX Settembre (SR 429), 23, 53017 Radda in Chianti. 39 320 802 9012.

La Bottega di Giovannino is more traditional and simple. Here they serve excellent, authentically-prepared food making it a great place to try ribollita (bean soup) or pici (a thick, hand-rolled pasta). Both dishes are Tuscan classics. This is one of our favorite place to eat lunch when in the area (with Giovannino Bernardon or one of his family choosing what we eat). The only downside is that you sometimes need to wait for a table. Open: 11:30AM – 10:30PM from Thursday to Sunday, 11:30AM – 3:30PM from Monday to Wednesday, and 6:00PM – 10:00PM on Wednesdays. Address: Via Roma, 6, 53017 Radda in Chianti. http://www.labottegadigiovannino.it/

For good, traditional pizza, head to Pizza Pie. There are only a few tables clustered near the main road, but both the quality and value are good. Open: 12:00PM – 3:00PM and 6:30PM – 9:30PM from Monday to Saturday. Closed on Sundays. Address: Viale 20 Settembre, 3, 53017 Radda in Chianti. +39 0577 738 758.

If you are staying at Il Borgo di Vèscine, you will probably eat there as it is 6 kilometers back to Radda. The good news is that they have a nice restaurant.

Things to Do

Sites

There are few formal “sites” as such in Radda – most of the charm is in just wandering the lanes and the walls.

Palazzo del Podestà is the 18th-century town hall (the original was destroyed by the French in 1478). Coats of Arms of local families cover the outside of the building. On the first floor there is a recently restored fresco of the 16th-century Florentine school. 

Lunch & Wine Tasting

Riding to lunch with optional wine tasting at Badia a Coltibuono gives you a real taste of Chianti. Just arriving up the tree-lined driveway to this one thousand years old abbey is a treat. The name literally means, “Abbey of the Good Harvest”. The Benedictines founded the abbey in 1051 and steadily expanded its vineyards. In 1810, when Tuscany was under Napoleonic rule, the monks were forced to leave. The estate is now owned by the Stucchi-Prinetti family but the tradition of producing great wines continues. Reservations for lunch recommended in high season. Located 10 kilometers east of Radda at the intersection of SR 429 and SP 408. Address: Loc. Badia a Coltibuono, Gaiole In Chianti. Open: 2:30PM – 5:30PM every day. +39 0577 74481. http://www.coltibuono.com/

The village of Volpai is another great excursion for food and wine – albeit with more climbing. Once a military lookout, this perfectly preserved village now is the tranquil setting for a great restaurant and winery. The Ristorante_La_BottegaRistorante La Bottega has a stunning setting and fantastic food. It has been in business for over 300 years, so they must be doing something right! +39 0577 735 602. Closed Tuesday. This ride is 15 KM there and back with 440 meters of climbing – mostly on the way out. To get to the start of SP 2bis you need to ride east from Radda on SR 429. You then ride over the top of SP 2bis then take the first exit at the roundabout to get onto SP 2bis. The Volpaia turn is a couple of KM further on, on your RHS. Open: 12:00PM – 3:00PM and 7:00PM – 10:00PM from Wednesday to Monday. Closed on Tuesdays. +39 0577 738001. http://www.labottegadivolpaia.it/  This trip can also be combined with a trip to the excellent Castello di Radda winery that you pass on the way up (closed on Sundays. +39 0577 738 992.)

To learn about wine tasting and food pairing, sign up for the Sommellerie Course at Hotel Relais Vignale. The course starts at 5:00 PM and takes about an hour. Address: Via Pianigiani, 9, Radda. +39 0577 738300.

Cooking Courses

The Hotel Relais Vignale runs a cooking course for a minimum of two people starting at 10:00AM. Address: Via Pianigiani, 9, Radda. +39 0577 738300.

For something a little more rural, there is an excellent half-day cooking class in nearby San Polo (between Radda and Lecchi) at the Toscana Mia Cooking School. The classes start at 9:30 AM or 4:00 PM. The classes are taught by two Italian sisters who have been giving cooking classes in their home since 1990. They also produce their own olive oil. Phone to make bookings and for directions. Address: Loc. Poggio San Polo, 2. +39 334 247 6098. https://www.toscanamia.net/

A little further down the SP 114/a, Simone at Restaurant Malborghetto (literally small bad village) in Lecchi runs a great cooking class from 9:30AM – 12:00PM. Closed on Tuesdays. €100 per person. Address: Via Monteluco, 4, Lecchi. +39 0577 746201 or +39 339 303 4871. https://www.malborghetto.net/

Useful Contacts

Tourist Information Office: Piazza Castello, 6, +39 0577 738494. In the small lanes off the main street (Via Roma) in the old town. Follow signs to “i informazione”. Staff at Italian tourist offices typically speak good English and are a great source of local knowledge and town maps.

Stores: You will find everything you need for a picnic at the excellent Porciatti Alimentari Piazza IV Novembre, 1-2-3. Located just outside the eastern gate of the old town. 8:00 AM to 1:30 PM and 4:00 PM to 7:30 PM. Mornings only on Sunday.

There is also a larger Coop outside of the city walls at the eastern end of town. Viale XI Febbraio, 1. +39 0577 735611. 08:30 AM to 1:00 PM and 4:00 PM to 8:00 PM. Closed Sunday.

A Little History

The area around Radda has been inhabited since 2000 BCE and the site of Radda was almost certainly an Etruscan village. By the fall of the Roman Empire in the 5th Century, Radda was a well-established village – along with the surrounding villages of Castelvecchi, Monterinaldi, and Volpaia.

In the 10th Century these villages became fortified with the rise of more feudal societies. By the 13th Century, the Radda territory had become a dependency of Florence. The castle was sacked by Siena in a raid in 1230 while in 1268 it was occupied, along with other locations in Chianti, by French troops led by Charles I of Anjou. It was again heavily looted during another French invasion in 1478.

In 1378, Radda became the headquarters of the Chianti League – a military alliance of the Florentine villages of Radda, Castellina and Gaiole. The leagues symbol – the black cock – is used to denote Chianti wine to this day. Like most of the villages in the area, Radda found itself in the middle of the interminable conflicts between Florence and Siena.  In 1550, Florence finally got the upper hand and relative peace came to the area.

By the 17th Century, these village-castles were defensive anachronisms and many were converted into elegant villas where the owners would, engage in the production of fine wine – some of it exported. More generally, for the next few centuries, Radda remained poor and isolated within the Grand Duchy of Tuscany.

Through much of the 1900s the town declined as people left the Tuscan countryside. However, with the rise of tourism, in the 1970s, the town saw a revival as the castles, villas and farmhouses of the area were restored and converted to hotels and B&Bs.

San Gimignano

Overview

While not much more than a village, San Gimignano is known as the “Medieval Manhattan” thanks to its many tall towers. The towers make for a memorable skyline, especially when approached along the twisting roadSan_ Gimignano width= from Ulignano.

In medieval times the great towers provided some defensive capability but were mostly built to boast of the importance of feuding nobles. Fourteen of the 72 original towers remain. The town is well preserved with little sprawl. It is also easily reached from both Florence and Siena so there are typically large numbers of day trippers. The good news is that most of these leave in the late afternoon leaving you with a quieter, more peaceful city to explore.

The town is centered on two linked squares: Piazza del Duomo and Piazza della Cisterna. The main street is Via San Matteo north of the squares and Via San Giovanni south of the squares. Clustered around these central squares are the following architectural highlights:

  • The Collegiata. A Romanesque cathedral. The name refers to the college of priests who originally managed it.
  • The Palazzo Comunale (civic museum) is an impressive 12th-century palace that was the center of government for the town.
  • The Torre Grossa (part of the Palazzo Comunale). Climb up for fantastic views of the city and the countryside beyond.

At the northern end of the city, Chiesa di Sant’Agostino is a 13th-century church situated on the pleasantly quiet Piazza San Agostino. The simplicity of this church is in marked contrast to others in the area. There is a Benozzo Gozzoli fresco illustrating the life of St Augustine behind the altar.

The town is also known for the white wine, Vernaccia di San Gimignano, produced from the ancient variety of Vernaccia grape which is grown on the sandstone hillsides of the area.

The town is a UNESCO World Heritage Site.

Eating & Drinking

If you are staying in San Gimignano: The ratio of day trippers to locals means that the quality of the restaurants are just OK. But OK in Tuscany, is quite good most other places.

Le Vecchie Mura has a nice terrace built into the town walls and vaulted ceilings in the converted stable inside. Food and service are generally good but you are going more for the great views and atmosphere. Open 6:00PM – 10:00PM from Wednesday to Monday. Closed on Tuesdays. Address: Via Piandornella, 15, 53037 San Gimignano. +39 0577 940 270. https://www.vecchiemura.it/

The restaurant at the Hotel Bel Soggiorno has consistently good food and nice views. Selection is wider than typical of the area with both local and international dishes. At the southern end of town on the main street – Via San Giovanni, 91. +39 0577 940 375. For dinner, reservation advised. Closed on Wednesdays.

Trattoria Chiribiri is a little away from the main tourist areas – up a small lane – so it is a little quieter than other restaurants especially at lunchtime. The food is OK though the service can go either way. Open: 11:00AMTrattoria_Chiribiri – 11:00PM every day. Address: Piazza della Madonna, 1/a – on the right just before the southern gate as you walk out of town on Via San Giovanni. +39 0577 941 948.

If you are staying outside of town, you will most likely eat at your hotel. All have good restaurants with the restaurant at La Collegiata being very good.

Sites and Things to Do

Sites

The Collegiata (AKA the Duomo). Address: Piazza Luigi Pecori, 1-2. Open: Monday to Friday from 10:00AM – 7.30PM, Saturday from 10:00AM – 5:30PM, and Sunday from 12.30PM – 7.30PM. Basilica di Santa Maria Assunta (the Duomo) and Chapel of St. Fina €4,00. Museum of Sacred Art€3,50. +39 0577 940316. http://www.duomosangimignano.it/

The Palazzo Comunale (AKA civic museum) and Torre Grossa. Address: Piazza Duomo, 2. Open 9.30AM – 6.30PM. Admission €6.00.

Chiesa di Sant’Agostino. Address: Piazza Sant’Agostino. Open 10:00AM – 12:00PM and 3:00PM – 7:00PM. Admission is free.

Useful Contacts

Tourist Information Office: In the center of the old town on Piazza Duomo. +39 0577 940008 Follow signs to “i informazione”. Staff at Italian tourist offices typically speak good English and are a great source of local knowledge and town maps.

Stores: There are plenty of small stores though the old town including La Buca di Montauto, which is good for picnic supplies. Address: Via S. Giovanni, 16. +39 0577 940 407. There is also a larger supermarket – a Coop – just outside the walls on the south side of the city. Address: Via Baccanella. +39 0577 943 072.

A Little History

In the 3rd century BC a small Etruscan village stood on the site of San Gimignano. In Roman times, the town was known as Silvia with the name changing to San Gimignano in 450 AD after Bishop Geminianus intervened to spare the castle-village from destruction by the followers of Attila the Hun. It was also, at times, known as the Castle of the Forest because of the extensive, now mostly vanished, woodland surrounding it.

In the Middle Ages and Renaissance era, San Gimignano was a stopping point for Catholic pilgrims on their way to Rome and the Vatican, sitting as it does on the medieval Via Francigena (a pilgrimage route from France to Rome). The city’s development was also improved by the trade in agricultural products from the fertile neighboring hills, in particular saffron (used in both cooking and for dyeing cloth) and Vernaccia wine, said to inspire popes and poets.

In 1199, the city declared itself independent of the bishops of Volterra (the prior rulers) and established a podestà. However, the peace of the town was disturbed for the next two centuries by conflict between the Guelphs and Ghibellines families. This resulted in the families building tower houses of increasing height. Towards the end of the Medieval period they were 72 in number and up to 70 metres (230 feet) tall. The tower building was finally constrained when the city council created an ordinance that no tower was to be taller than that adjacent to the Palazzo Comunale – the Torre Grossa.Torre_Grossa

The city flourished until 1348, when it was struck by the Black Death that affected all of Europe, and about half the townspeople died. The town then submitted to the rule of Florence. Initially, some Gothic palazzo were built in the Florentine style, and many of the towers were reduced to the height of the houses. There was little subsequent development, and San Gimignano remained preserved in its medieval state until the 20th century, when its status as a touristic and artistic resort began to be recognized.

Sovicille

Overview

SovicilleSovicille is more a stop on a journey than a destination in itself and you won’t find it in most tourist guides to the region. Sometimes, following the route less travelled, is one of the pleasures of touring by bike! That said, the town of Sovicille has a quiet charm with a pleasant and well-preserved central old town that can trace its roots back to 1000 CE. It also has a Roman mosaic and has been variously ruled by the Florentines, the Sienese, the Medici family and even the French.

Eating & Drinking

Where you eat will depend largely on where you are staying. If you are staying at Tenuta la Santissima, you are lucky – you will be very well fed by your hosts (advanced notice needed).

If staying at Relais Borgo di Toiano the hotel can prepare very simple dinners of antipasti, salads, and sandwiches by prior arrangement. However what they usually do is drive guests to a local restaurant.

Alternatively, about one kilometer away (down a quiet but unlit lane) is Il Ristoro di Ponte allo Spino. It is not too much to look at but they serve good food – like wild boar stew as well as pizza and pasta. Open: 12:00PM – 2:30PM and 7:00PM – 10:00PM every day. Address: S.P.37 delle Volte Basse 20, 53018 Sovicille. +39 0577.314307. To get there head back down the road you arrived on. The restaurant is at the end of the road, where it joins SP 37.

With a taxi you can get to the excellent Osteria Nonno Giulio. This country inn is set in the woods and specializes in country Tuscan cooking. The gnocchi with saffron and fettuccine with wild boar sauce are both great. Open: 7:00PM – 11:00PM Thursday to Tuesday, and 12:00PM – 4:00PM on Sundays. Closed on Wednesdays. Address: Str. di Piscialembita, 70, 53018. +39 0577 314 152. Located 3½ kilometers back down the route you arrive in on at Strada di Piscialembita, 70 – on RHS before you get to Ancaiano. Ask your hotel to arrange a taxi.

Useful Contacts

Tourist Information Office: Via Roma, 27 Sovicille. +39 0577 314503. Follow signs to “i informazione”. Staff at Italian tourist offices typically speak good English and are a great source of local knowledge and town maps.

Stores: If you want to collect picnic supplies for you next day’s ride, we would suggest waiting until you are en route. One of the first stores you will come to is La Bottega on the LHS of the main street in Ville di Corsano.

A Little History

The name Sovicille is documented as far back as 1004 but the origins of the place probably go back much further. In 2002 a mosaic from the Roman period was uncovered in the Church of St John the Baptist and there is no shortage of Etruscan relics in the immediate area. The name itself is thought to derive from the Latin words “sub” and “ficinulae/ficus” (small fig tree).

The history of Sovicille is not particularly interesting in and of itself. However, in many ways, it is representative of what happened to many Tuscan villages and cities: batted back and forth between Volterra, Siena and Florence. Taken over by feudal families and then invaded and controlled by the French before becoming part of modern-day Italy.

In longer form …

During the Middle Ages the region found itself on the borders between Siena and Volterra: The Abbey of Serena, some 30 kilometers to the west, was under the control of Volterra, and the land around Sovicille was included as property of the abbey around the year 1000.

In the thirteenth century the democratically administered Republic of Siena allowed Sovicille (and a number of other municipalities) their own municipal statutes. However, in 1260 Sovicille was occupied by Florence but then returned to Siena after the Florentine armies were defeated at the Battle of Montaperti. In 1333 Sovicille was overrun and burned down by Pisa.

The Medici family purchased the lands of Siena from the Emperor for two million ducats in 1557: this was followed by the abolition of democratic institutions and a return to feudalism and Sovicille became a fief of the Medici family who transformed it into an imposing fortress, defending an access point to their newly expanded territories.

After the death of the last of the Medici rulers, power transferred to the Dukes of Lorraine who remained in control till the end of the eighteenth century when the entire region was invaded by Napoleon Bonaparte. The French remained in charge till 1814 when, under the terms agreed at Vienna, Sovicille was annexed to the Grand Duchy of Tuscany. In 1859 it came under the control of the short-lived United Provinces of Central Italy, which was effectively a transitional entity leading to incorporation in 1861 within the new Kingdom of Italy.

Request Itinerary

Day-by-Day

Castelnuovo Berardenga to Radda

Overview

Most people start today with a van transfer from Siena or Florence to Castelnuovo Berardenga – Chiantiat the southern limit of the Chianti wine region. Despite the name, the town dates back to the 1300s though the large villa and gardens – Villa Chigi Saracini – you see as you approach the town date only from the 19th Century. The pleasant-though-unremarkable town is worth a quick loop before moving on.

The Intermediate route starts with a gentle three-kilometer descent across rolling countryside. This pastoral terrain is in contrast to the more rugged landscapes found in northern Chianti. Soon after leaving Castelnuovo, you see the iconic towers of Siena across the valley.

After San Piero, you start a long climb on a remote road across to Castello di Brolio. The land here is carpeted with vines and the roads are lined with olive trees. Castello di Brolio dates back to the 12th Century and is one of the most stunning castles in Tuscany. It also has an excellent winery that claims to be the birthplace of the iconic Chianti wine. The Ricasoli family has lived Chiantihere since 1141 and is still in residence so access is restricted to the gardens, chapel and museum – but is still a good visit though you need to ride one kilometer up a gravel road to reach it. The winery – down on the main road – is also worth a stop, if it is not too early to taste wine. Brolio is also where the Easiest route begins.

From Brolio, you have a sweeping descent before a gentle climb up to Gaiole – where most people doing the Intermediate and Easiest rides have lunch. (Those doing the challenge ride will head up to San Sano or Lecchi for lunch.)

As well as being a nice place for lunch, Gaiole has good gelato and an interesting bike store -selling retro bike gear.

The ride from Gaiole to Radda includes a 5-KM climb but the road is well graded with a good surface so typically not too stressful. Just before you reach Radda, you pass Rampini Ceramics – a good stop for anyone interested in hand-painted tableware. The final kilometer to the walled city of Radda is relatively steep: the sting in the tail!

Route Options

The route described above – and in your turn-by-turn directions – is the Intermediate Route.

Easiest Route

If you want to reduce the amount of riding (and climbing) that you do, asked to be transferred to Brolio Castle to start your ride here. You then follow the Intermediate Route – see profile for the intermediate route, below.

If you have a late arrival, or just want to reduce the amount you ride even more, ask to be transferred to Gaiole. This reduces the ride to 12 KM with 250 meters of climbing.

Intermediate Route

Like most of Tuscany, you are always climbing or descending but the hills – for the most part – are not too long and not too steep. The exception is the final climb up to Radda, which is a steady five-kilometer climb – though well graded on a nice surface.

Challenge Route

For a more challenging ride – and some alternative lunch options – you ride up to Radda on the quiet-but-steep road that goes through Lecchi. There is a great lunch option in Lecchi as well as a nice one in San Sano (just off the route).

Epic Route

For an even more challenging ride – with steep climbs and technical descents – you ride north of Castelnuovo Berardenga to the pretty village of San Gusmé. From here you have a 10-KM climb with fantastic vistas up to the TV tower at Monteluco followed by a twisting-and-technical descent through Castagnoli and past the Castello di Meleto winery. After a brief respite from the hills, you start climbing again up the quiet-but-steep road that goes through Lecchi. There are good lunch options in Castagnoli, Lecchi and San Sano (just off the route).NOTE: this is a strenuous ride in remote countryside. Given this is your first day, if you are not used to cycling steep hills and acclimatized to the heat, you should not attempt this ride.

Lunch

There are many good places to eat lunch today. Where you choose will depend on your route.

On the Intermediate and Easiest Routes, your first lunch option is the Osteria del Castello at Brolio Castle. The food is respectable though the restaurant can get crowded with crowds from tour buses. Located on the RHS 200 meters up the road to the Castle. Open every day from April 1stto November 2nd from 12:00    PM – 2:30PM and 7:00PM – 10:00PM. +39 0577 730 290. https://ricasoli.com/osteria/

In Gaiole, there are a couple of good options.

The best atmosphere is on the pedestrianized piazza at Lo Sfizio Di Bianchi – watch the world go by as you enjoy pasta or pizza. They also have good gelato. Open every day from 7:30AM – 11:00PM. Address: Via Ricasoli, 44/46. +39 0577 749501. http://www.losfiziodibianchi.it/

The food, however, is a little better at Osteria al Ponte – across a small bridge, on the RHS as you ride into town. Eating outside on the vine-shaded patio is a pleasure not to be rushed. Open 12:00PM – 2:30PM and 7:00PM – 10:30PM every day. Address: Via Antonio Casabianca, 25. +39 0577 744 007.

The best food (and the highest prices) in town is found at the hotel Castello di Spaltenna. In summer, they serve an excellent lunch on the terrace in their La Terrazza Restaurant. Open every day. Turn left in the center of Gaiole, signed “Vertine 3.” After 300 meters turn left, signed to “Ristorante il Pievano al Castello di Spaltenna.” Address: Via Spaltenna, 13. +39 0577 749 483. https://www.spaltenna.it/en/home

In Lecchi: the Restaurant Malborghetto (literally small bad village) is a great restaurant
serving inventive food, nicely presented by the chef/owner, Simone. In the past he has taken a look at our riders and declared, “I know just what you need to get you up the hills” and proceeded to serve delicious pasta. They also have a cooking school in the mornings until 12:00PM. Open: 12:00PM – 2:30PM and 7:00PM – 9:30PM. Closed on Tuesdays. In the center of Lecchi, take a sharp right turn up a small lane – signed). Address: Via Monteluco, 4, 53013 Lecchi in Chianti. +39 339 303 4871. https://www.malborghetto.net/home-en/

Also in Lecchi (on the RHS in the center), Enoteca Rinaldi is a wine bar that serves espresso and light lunches. Open “all day”, every day. Address: Via S. Martino, 9/5, 53013 Lecchi in Chianti.

In San Sano: Trattoria La Grotta della Rana in this tiny hamlet is a village restaurant in the best traditions of Tuscany. You will find well-prepared Tuscan favorites here in a congenial setting. There is seating both inside and outside under a large awning. Open: 8:00AM – San_Sano10:00PM Thursday to Tuesday. Closed on Wednesdays. +39 0577 746020. [NOTE: San Sano is on a side road: a left turn shortly before Lecchi.] Address: Via Padre Cristoforo Chiantini, 53013 San Sano.

In Castagnoli, the Osteria il Bandito is simple, family-run hill town restaurant with friendly service and good food. Open: 12:00PM – 2:30PM and 7:00PM-9:00PM every day. Located at the intersection of SP 77 and SP 73/b as you arrive into Castagnoli. Address: Localita’ La Croce, 5, 53013 Castagnoli. +39 0577 1698218. http://www.osteriailbandito.com/

In Ama: Il Ristoro di Ama is part of the winery and has excellent food and a pleasant patio. As you might expect, they specialize in pairing wines with the food. Reservations needed. Open: 12:00PM – 2:30PM and 7:00PM – 9:00PM. Closed on Tuesdays. Address: Ama, Località Castello Di, 53013 Gaiole in Chianti. +39 0577 746 031. https://www.castellodiama.com/en/

Wineries en Route

There are numerous small wineries on today’s route with three world class producers.

Castello di Brolio is perhaps the most storied winery on today’s route – it is also part of one of the most stunning castles in the region. The Ricasoli family has owned the property since 1141 Ricasoli_wineryduring which time it has been rebuilt and remodeled several times. The family business, Barone Ricasoli, is the fourth oldest company in the world and the second oldest in the wine sector (Château de Goulaine in the Loire Valley is said to be older). This is the place where the distinctive Chianti wine was invented. Not surprisingly, their wines are very good too! Mon thru Fri 9:00 AM to 7:30 PM, Sat & Sun 11:00 AM to 7:00 PM. +39 0577 7301. https://booking.ricasoli.com/eng/

Castello di Meleto is another fairytale castle in, perhaps, an even more beautiful setting; just off the described route perched atop a hill above Gaiole. The 2,470-acre estate produces Chianti classico, spumante brut rosè and grappa. The farm also produces an excellent extra virgin olive oil and, to round out the story, they also breed cinta senese pigs. Several tours available – call ahead for times (typically 11:30 AM and 4:30 PM). +39 0577 749129. https://www.castellomeleto.it/

Castello di Ama is set in a charming village – a left turn near the top of the hill after Lecchi. Like the other wineries on today’s route, it’s worth visiting for the setting alone. As well as great Chianti wines, the winery produces good crus, vin santo and their own olive oil. Open from 11:00 AM to 8:00 PM daily. Reservations essential. +39 0577 746 069. https://www.castellodiama.com/en/

Casanuova di Ama is an altogether more casual and down-to-earth winery even though their grapes are grown on the same “hills of Ama” as their more prestigious neighbor. They have a pleasant garden where you can taste their good and well-priced wines – without an appointment. Truly classic Chianti wines from the heart of the Chianti region. In our opinion it is worth splurging on the riserva (at €15) as well as taking the chance to try their vin santo and olive oil. Located down the next left turn after the Castello di Ama turn along SP 114/A. +39 0577 746 119. Closed Sunday. http://www.agrariacasanuovadiama.it/


The Black Rooster

From the fourteenth century on the Black Rooster became the symbol of the military league of Chianti, set up in 1394 to defend the local territory around Radda, Gaiole and Castellina.

It was set up as a defensive community, under the auspices of the Florentine State, boasting its own militia, its own statute and the special insignia: a black rooster on a yellow background.

As the wars between Florence and Siena came to an end, the League focused on controlling the viticulture of the area. A role that the League continues to play to this day.

Statutes describes the League as a company of free men [sic], brought together by non-profit motives, to pursue specific aims, foremost among which is the enhancement and validation of the area of Chianti.

The ceremony used for swearing in the leaguers is: “I promise to remain close to nature, to give my life a religious sense, to look around me with optimism and love, and at least once a year to make a loving gesture towards my fellow men”.


Useful Contacts en Route

Stores: The largest store on route is the Coop at the northern end of the pedestrianized piazza in Gaiole. If you are planning a picnic lunch, note that they close at 12:45 PM and don’t reopen until 4:30 PM. There are several other small food stores and wine bars on the piazza. Address: Via Bettino Ricasoli, 102/104/106, 53013 Gaiole In Chianti.

Lecchi has a small store, a wine bar (Enoteca Rinaldi where Paolo serves a great espresso and simple lunches) and a more traditional café/bar.

Ceramics: For those interested in ceramics, Rampini Ceramics – south of Radda on SP 2 – produces handmade and hand painted traditional pottery. This is the workshop that supplies their store in Florence. +39 0577 738043.

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Radda Loop Rides

Overview

The Intermediate route today east to Badia Coltibuono – a beautifully located converted abbeyRadda that dates back to 1051. The monks left the abbey in 1810 and the property is now a hotel, winery and restaurant. The gardens are also worth a visit. If you make a late start, this is a nice place for lunch.

From the abbey, you enjoy a fast, twisting descent into Gaiole. Gaiole is a classic, rugged Chianti market town with a cluster of shops and restaurants. Much of the town’s character comes from its location – nestled in a steep-sided valley alongside a fast-flowing river. Historically, it has been a marketplace rather than a place of defense and is not fortified. Indeed, during the battles between Florence and Siena the center was destroyed and rebuilt several times. The center of the town is dominated by a large triangular-shaped “square”. If you are lucky, you will pass through on market day or during one of the many art, food, or wine festivals. Gaiole also has a great bike shop selling retro bike gear. This is where the famous L’Eroica bike race starts. NOTE: The GPS route take you through a pedestrianized zone in Gaiole. Please walk your bike on this section.

Depending on when you start your ride, Gaiole can make a great coffee or gelato stop. If you had lunch here yesterday, you may choose to push on to San Sano or Lecchi before stopping to eat.

After Gaiole, you enjoy a gentle decent alongside the Massellone River. Castello di Meleto is just a short detour off the route here. After some gentle descending, you turn right towards Lecchi. Shortly before Lecchi, there is a pleasant two-kilometer side trip to the pretty village of San Sano – a great place for lunch (see Lunch section below).

From San Sano the terrain gets more arid and the roads a little more isolated. The route climbs steadily through Lechhi where the road is barely wide enough for a large car to pass between the houses. The climb continues past Castello di Ama – a small hamlet dominated by a winery and restaurant of the same name (and a spectacular lunch option). The pastoral setting and cobble-stone lanes make this a worthy detour and scenic resting point on the climb up to Radda.

From the Castello di Ama turn, the road flattens out before a three kilometers descent followed by a final, three kilometers, climb up the walled city of Radda in Chianti. You have fine views of your destination as you make this final ascent.

Route Options

The route described above – and in your turn-by-turn directions – is the Intermediate route.

Intermediate Route

The climb up to Lecchi is the major challenge on this ride – a steady four-kilometer climb with the grade pitching up above 10% for short sections.

Easiest Route

The Easiest route follow the Intermediate route to Gaiole. However, as you head south of Gaiole, you take a right turn up the SP 2, rather than the longer-and-steep route via Lecchi. Note, if you rode this route yesterday, you will be repeating the ride into Radda.

Challenge Route

The Challenge route is a stunning ride and well worth the effort – if you are comfortable with extended climbs. However, the amount of climbing makes this a tough ride.The ride from Radda begins with a steep descent down an old lane that eventually runs alongside a small stream before starting the steady climb up to Panzano. Set atop a hill surrounded by classic Tuscan countryside, Panzano is a scenic stop. Lovers of meat might want to visit Italy’s “most famous” butcher’s shops – Antica Macelleria Cecchini. This extraordinary store includes wines tastings, art shows and, on occasion, concerts. The proprietor, Dario Cecchini, also has a number of carnivore-centric restaurants clustered around the store.The route takes you through the historic center of Panzano – under an arch and up to the church of Santa Maria A Panzano. The church is relatively modern by local standards (19th-century) but contains a 14th-century Madonna and Child attributed to Botticini.

After Panzano, it’s back onto quiet lanes that twist and turn – sometimes very steeply –through the hills before starting a long, technical descent down towards Greve. Shortly before Greve, the village of Montefioralle is one of the oldest in Chianti. It was originally built as a fortified Montefioralle<a href=” width=”300″ height=”226″ />monastery in the tenth century then, in the Middle Ages, it became a military base. The, otherwise unremarkable, church of San Stefano houses a thirteenth century depiction of the Virgin. The town’s two trattorias are both great choices for lunch.

The descent continues from Montefioralle into the bustling market town of Greve. This is the topological low point of the ride but is a pleasant stop and a good place to refuel with snacks and fill water bottles before the hilly ride back to Radda. The main “square” – actually more an irregular triangle – hosts a market on Saturdays but on other days it is also worth a wander around. This piazza is fronted by numerous medieval aged buildings, including the 11th-century Chiesa Santa Croce which was rebuilt in 1325 after being burned to the ground, along with the rest of the town, by the Duke of Lucca, Castruccio Castracani. The statue in the center of the piazza honors Giovanni da Verrazzano (1485–1528) the first European to discover New York Bay in 1524. The bridge over the opening of New York Harbor is named after him.

From Greve, the riding gets a little more serious and the terrain hillier and more isolated. However, the quiet roads and expansive views make it worth the effort. Lucolena and Badia a Montemuro are small villages on the route that offer the chance to rest and catch your breath. The latter of these also has a great osteria – perfectly positioned if you made an early start. The ride also peaks just before Badia a Montemuro where the views open up and you get magnificent vistas towards Radda and beyond as the road pitches and rolls steeply requiring care in the corners.

After nearly eight kilometers of descending, your ride ends with a two-kilometer steep climb back up to Radda – the sting in the tail!

Epic Route

The Epic ride starts out the same as the Challenge ride until Panzano. Then, when riding on SP 118 out of Panzano, rather than making the Montefioralle turn, you continue straight to Mercatale and then onto Strada in Chianti. From Strada, there is a beautiful, and twisty, road (SP 66) that brings you back to the Challenge route shortly before Dudda.

For this route, we recommend using a GPS unit or loading the GPS files onto a smart phone.

ALTERNATIVELY: For a short in-and-out ride: head north of Radda to the scenic hill town of Volpaia. Once a military lookout, this perfectly preserved village now is the tranquil setting for a great restaurant and winery. There is also a wine bar/café and a good osteria. This ride is 15 kilometers with 440 meters of climbing. Ride east from Radda on SR 429. You then ride over the top of SP 2bis then take the first exit at the roundabout to get onto SP 2bis. The Volpaia turn is a couple of kilometers further on, on your RHS.

Lunch

Where you choose will depend on your chosen route. It is also worth checking below which days the restaurants are closed to avoid disappointment.

Badia a Coltibuono, just north of Gaiole, is a converted Abbey with a great combination of food, wine, views and history. Open seven days a week, 12 AM to 2:30 PM for lunch. 7:00 PM to 9:30 PM for dinner. +39 0577 74481. https://www.coltibuono.com/en/restaurant/

In Gaiole, there are a couple of good options.

The best atmosphere is on the pedestrianized piazza at Lo Sfizio Di Bianchi – watch the world go by as you enjoy pasta or pizza. They also have good gelato. Via Ricasoli, 44/46. +39 0577 749501. Closed Wednesday. http://www.losfiziodibianchi.it/

The food, however, is a little better at Osteria al Ponte – across a small bridge, on the RHS as you ride into town. Eating outside on the vine-shaded patio is a pleasure not to be rushed. Address: Via Antonio Casabianca, 25. +39 0577 744085. Closed Monday.

The best food (and the highest prices) in town is found at the hotel Castello di Spaltenna. In summer, they serve an excellent lunch in the terrace: in their La Terrazza Restaurant. Turn left in the center of Gaiole, signed “Vertine 3.” After 300 meters turn left, signed to “Ristorante il Pievano al Castello di Spaltenna.” Via Spaltenna, 13. +39 0577 749 483. https://www.spaltenna.it/en/restaurants/la-terrazza

In Lecchi: the Restaurant Malborghetto (literally small bad village) is a great restaurant serving inventive food, nicely presented by the chef/owner, Simone. In the past he has taken a look at our riders and declared, “I know just what you need to get you up the hills” and proceeded to serve delicious pasta. In the center of Lecchi, take a sharp right turn up a small lane – signed. They also have a cooking school in the mornings until 12:00. +39 0577 746201. Closed Tuesday. Address: Via Monteluco, 4, 53013 Lecchi in Chianti. https://www.malborghetto.net/home-en/

Also in Lecchi (on the RHS in the center), Enoteca Rinaldi is a wine bar that serves espresso and light lunches.

In San Sano: Trattoria La Grotta della Rana in this tiny hamlet is a village restaurant in the best traditions of Tuscany. You will find well-prepared Tuscan favorites here in a congenial setting. There is seating both inside and outside under a large awning. +39 0577 746020. Open Thursday to Tuesday from 8:00AM – 10:00PM. Closed Wednesdays. [NOTE: San Sano is on a side road: a left turn shortly before Lecchi.] Address: Via Padre Cristoforo Chiantini, 33, 53013 San Sano. http://www.lagrottadellarana.it/

In Ama: Il Ristoro di Ama is part of the winery and has excellent food and a pleasant patio. As you might expect, they specialize in pairing wines with the food. Reservations needed. +39 0577 746 031. Open Wednesday to Monday from 12:00PM – 2:30PM and 7:00PM – 9:00PM. Closed Tuesdays. +39 0577 746191. Address: Ama, Località Castello Di, 53013 Gaiole in Chianti. https://www.castellodiama.com/en/

In Panzano, carnivores should head to one of Dario Cecchini’s carnivore-centric restaurants clustered around his butchers shop – Antica Macelleria Cecchini. Dario Doc – above the store – serves the famous Mac Dario claimed to be the best burger in Italy; and they could just be right. Amazingly, they also have a vegetarian menu! Open: 9:00AM – 4:00PM every day. Just off SR 222 at Via XX Luglio, 11. +39 055 852020. Address: Via XX Luglio, 11, 50022 Panzano In Chianti. https://www.dariocecchini.com

In Montefioralle, there are two great family-run trattorias.

La_CastellanaLa Castellana, is a small restaurant that has indoor seating as well as a shaded patio on the opposite side of the road. Excellent, traditional Tuscan food at reasonable prices. Open Tuesday to Sunday from 12:30PM – 2:30PM and 7:30PM – 9:15PM. Closed Monday. Located 50 meters beyond Montefioralle towards Greve. Address: Via Montefioralle, 2, 50022 Greve in Chianti . +39 055 853134. Closed Monday.

For stunning views, rustic setting and authentic dishes head to Taverna del Guerrino in the heart of the village. A true family affair run by Marco Niccolai with his mother and wife Gabriella. Open from Tuesday to Sunday from 12:15PM – 3:00PM and 7:15PM – 10:00PM. Closed Monday. +39 055 853 106. Address: Via Montefioralle Centro, 39, Greve in Chianti. https://www.ilguerrino.com/

In Greve, there are many choices for eating in Greve – most located around the main “square” and most are good. Of note, Mangiando Mangiandois a pleasant osteria serving good local food with nice service. Open from Friday to Wednesday from 12:00PM – 3:00PM and 7:00PM – 10:00PM. Closed Thursdays. Address: Piazza Giacomo Matteotti, 80, 50022 Greve in Chianti. +39 055 854 6372. http://www.mangiandomangiando.it/

In Badia a Montemuro Osteria del Rifugio del Chianti is one of our favorites in the area. It is welcoming and unpretentious with conscientiously prepared food. There is also a nice outdoor seating area where you are as likely to be sitting next to local farmers as tourists. Open from Thursday to Tuesday 11:00AM – 2:30PM and 5:00PM – 9:00PM. Closed on Wednesdays. Located 50 meters off the main route in Badia a Montemuro. Address Localita’ Montemuro, 12, 53017 Radda in Chianti.

In Volpaia, the Ristorante La Bottega has a stunning setting and fantastic food. It has been in business for over 300 years, so they must be doing something right! Open Wednesday to Monday from 12:00PM – 3:00PM and 7:00PM – 10:00PM. Closed Tuesdays. +39 0577 738001. http://www.labottegadivolpaia.it/homepage.php

The Osteria Volpaia, in the center of the village, is a good backup when the Bottega is closed. Open from Thursday to Tuesday from 12:00PM – 2:00PM Address: Localita’ Volpaia, 53017 Radda in Chianti. +39 0577 738 066. https://www.osteriavolpaia.com/

For something a little more casual and better-priced, the popular Bar Ucci has great Tuscan food served on its pleasant patio right in the center of town. Piazza della Torre 9. +39 0577 738 042.

Wineries en Route

There are a few smaller wineries on today’s route and a couple of more major destinations:

VolpaiaThe tasting room (Bioenoteca) for the winery in Volpaia is in the center of the village featuring both wines and olive oil. +39 0577 738 066. Open 10:30 AM – 6:00 PM. Closed Wednesday. Address: Loc. Volpaia 53017 Radda in Chianti. +39 0577 738066. http://wine.volpaia.com/

Castello di Radda is just north of Radda on the LHS on road up to Volpaia. Open 10:30AM – 5:30PM Monday to Saturday. Closed on Sundays. Address: Località Il Becco, 101/a, 53017 Radda in Chianti. +39 0577 738 992. http://www.castellodiradda.com/en/

Castello d’Albola is set in a tiny medieval village high up in the Chianti hills – south of Radda on SP 72. The magnificent views alone justify the stop. Despite the setting, the winery itself is relatively new and claims, “to have a Chianti Classico that is contemporary without being international.” Open: Friday to Monday from 10:00AM – 6:00PM. Address: Via Pian d’Albola, 31, 53017 Radda in Chianti. +39 0577 738 019. https://www.albola.it/

In Greve, there are numerous places selling wine. One good place for a relaxed but well-informed tasting is Enoteca di Greve. Address: Viale Vittorio Veneto, 112/a. + 39055 854 6209. https://www.enotecadigreve.it/who-we-are Another good outlet is Enoteca Del Gallo Nero. Closed on Thursdays. Address: Piazza Santa Croce, 8. +39 055 853297. http://enoristorantegallonero.it/en/

Near Gaiole, Badia a Coltibuono is an exceptionally pleasant winery in the tiny, 1000-year-old hamlet of the same name. The name means Abbey of the Good Harvest and today they live up to that name – at least in respect of the harvest. They have daily guided tours, including the tasting of 2 of their wines. They also have a great restaurant sited on a shaded terrace. +39 0577 74481. Open daily. https://www.coltibuono.com/en/wine-tasting-chianti/

Castello di Meleto is another fairytale castle in, perhaps, an even more beautiful setting; just off the described route perched atop a hill above Gaiole. The 2,470-acre estate produces Chianti classico, spumante brut rosè and grappa. The farm also produces an excellent extra virgin olive oil and, to round out the story, they also breed cinta senese pigs. Several tours available – call ahead for times (typically 11:30 AM and 4:30 PM). +39 0577 749129. https://www.castellomeleto.it/

Castello di Ama is set in a charming village – a left turn near the top of the hill after Lecchi. Like the other wineries on today’s route, it’s worth visiting for the setting alone. As well as great Chianti wines, the winery produces good crus, vin santo and their own olive oil. Open from 10:00 AM to 6:00 PM daily. Reservations essential. +39 0577 746 069. https://www.castellodiama.com/en/

Casanuova di Ama is an altogether more casual and down-to-earth winery even though their grapes are grown on the same “hills of Ama” as their more prestigious neighbor. They have a pleasant garden where you can taste their good and well-priced wines – without an appointment. Truly classic Chianti wines from the heart of the Chianti region. In our opinion it is worth splurging on the riserva (at €15) as well as taking the chance to try their vin santo and olive oil. Located down the next left turn after the Castello di Ama turn along SP 114/A. +39 0577 746 119. Closed Sunday. http://www.agrariacasanuovadiama.it/

Useful Contacts en Route

Stores: There is a large supermarket in Greve: the Coop is on the main route – on the LHS as you ride down the main road, SR 222. Open Monday to Saturday from 8:00AM – 1:00PM and 4:00PM – 8:00PM. Closed on Sundays. Address: Viale Vittorio Veneto, 76, 50022 Greve in Chianti.

Panzano has some smaller stores, good for drinks and snacks.

Butchers: Antica Macelleria Cecchini is Italy’s most famous butchers. They also have snacks and drinks. Open: 9:00 AM – 4:00 PM every day. Address: Just off SR 222, Via XX Luglio, 11, 50022 Panzano In Chianti. https://www.dariocecchini.com/en/

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Radda to San Gimignano

Overview

Today you transition from compact Radda to imposing San Gimignano – known as the “Medieval Manhattan” thanks to its stunning skyline of towers. This is a transition that takes you through several landscapes: forests, open valleys and large, rolling San_Gimignanohills.

The Intermediate Route starts with a ride along the ridge that joins Radda to Castellina in Chianti. Castellina – like so many Tuscan towns – is situated atop a hill. It sits at the crossroads of ancient routes that crossed the Arbia, Elsa and Pesa valleys. It also sits on the Chiantigiana road that connects Florence to Siena. A short detour takes you down the pleasant main street and around the pedestrianized historic center. Some of the lanes run under the buildings. Castellina also has an excellent gelato store.

From Castellina, you head northwest along another ridge towards San Donato. Before reaching San Donato, you turn left down a series of small lanes that pitch up and down as you saw-tooth your way across rolling farmland before arriving into Barberino. Barberino is a peaceful and pretty town and it is well worth a detour of the main route to visit the old town (Centro Storico). It is also the most logical place for lunch having a couple of good supermarkets and decent restaurants.

From Barberino it is back onto the small lanes with plenty of descending and a couple of easy-to-miss turns so watch your odometer. A side trip to Sant’Appiano is only worth it for aficionados of 10th-century churches. There are also Etruscan tombs dating back to the 8th century BCE but little to see and the church is typically closed except on Sundays. However, the simplicity of the church is in pleasant contrast to some of the more elaborate structures found in the area. Some claim it is the oldest church in Chianti – a confusing title as most churches have had some level of rebuilding but it does have Etruscan origins.

San_GimignanoFrom here, you descend further to the tiny town of Vico. Hardly a blip on the map, this is the last reasonable place for supplies before San Gimignano. The small lanes may also have you wondering if you have taken a wrong turn!

After crossing the main highway (SR 429) you climb steeply through the unremarkable town of Ulignano – unremarkable except for the fact that the road is so steep! Soon after Ulignano, you get your first views of San Gimignano and its towered skyline. After a few kilometers of relief from the climbing, you then have the last climb of the day up to San Gimignano. The sight of the majestic towers in the distance might help take your mind of your legs.

Route Options

The route described above – and in your turn-by-turn directions – is the Intermediate route.

Intermediate Route

Overall, the ride downhill but with nearly 900 meters of climbing, it does not always feel that way. We class this as an intermediate ride but the five kilometers of climbing at the end of the ride can make it feel quite challenging. The route is tricky to follow in some place but our objective is to avoid the commercial sprawl of Poggibonsi.

Easiest Route – Option 1

The simplest way to make this an easier ride is to ask for a transfer partway along the route – most people choose Barberino. This reduces the ride by 30 KM and saves 470 meters of climbing.

Alternative transfer points are as follows:

  • Castellina: 35 KM / 670 meters,
  • Ulignano: 10 KM / 270 meters.

See the Intermediate ride above for the ride profile.

Easiest Route – Option 2

Another option to make this a somewhat easier ride is to take SP 130 from Castellina into Poggibonsi. You then cross Poggibonsi to SP 95 and on to Ulignano where you rejoin the described route.This reduces the distance by 10 KM and saves 250 meters of climbing. However, while you save some climbing the route requires you to navigate through the busy and commercial Poggibonsi. Only choose this option if you are comfortable navigating across (and possibly getting lost in) a medium-sized city.

Epic Route

From Radda, follow the route marked on the map to San Casciano. From here you head southwest towards Montespertoli and onto Castelfiorentino, and Certaldo.

This ride requires some careful navigation, through Castelfiorentino. If you are riding this epic route we recommend using a GPS unit or loading the GPS files onto a smart phone.

Lunch

There are plenty of lunch options in Castellina but you will probably want to push further along the route before stopping to eat. Barberino makes a more logical stopping points.Barberino

In Barberino: The best traditional option is Osteria Il Campanellino. The restaurant has a nice terrace near the church with good views. You get to it down a couple of flights of steps down the side of the church off the main square. Open from 12:30PM – 3:00PM every day although that can be slightly unreliable. Address: Piazzetta Spedale dei Pellegrini, 36, 50021 Barberino Val D’elsa. +39 0558 075 770. http://www.osteriailcampanellino.it/

If Osteria Il Campanellino is closed, L’Archibugio is a good alterative if you like pizza (their other dishes tend to be less good). Located just the other side of the church from Osteria Il Campanellino. Open from 12:00PM Wednesday to Monday. Closed on Tuesdays. Address: Via di Bustecca, 10, 50021 Barberino Val D’elsa. They also have a nice terrace. +39 0558 075 209. http://www.pizzerialarchibugio.com/

On the small main square (Piazza Barberini) – halfway along the main street through the old town – the charming Il Canto di Baccio is a small store selling organic products. They also serve bruschetta, cheese and salami plates at a couple of tables just outside the shop. Great for a light lunch or picnic supplies. Address: Piazza Barberini, 3, 50021 Barberino Val D’elsa. +39 055 807 5131.

BarberinoAlso on the main square – but not always open for lunch – Cafe’ Bijou serves simple pizza and pasta in a lively environment. Open from 10:30AM, every day. Address: Via Francesco da Barberino 33. +39 392 584 8889.

There is also a good Coop supermarket at the southern edge of town where your route meets SR 2.

Other Options: If you are riding on Sunday, Sant’Appiano makes a nice side trip both to see the church and to have lunch at Osteria l’Antica Quercia. This country tavern has a pleasant outdoor terrace and well-prepared local food including pizza. Open for lunch on Sundays only. Address: Via, Str. di S. Appiano, 33B, 50021 Barberino Tavarnelle. +39 055 807 5281.

Wineries en Route

There are no major wineries on today’s route but a handful of smaller establishments including:Casa_Emma

Just south of San Donato, Casa Emma is a modern winery (opened in 1970) in a nice setting. They have a good selection of strong Chiantis as well as an interesting merlot and their showcase soloìo. They also have a restaurant though there are reports of them being unfriendly to cyclists. Open from 9:00AM every day. Address: Strada Provinciale Castellina in Chianti. +39 055 807 22 39. http://www.casaemma.it/

Shortly before Barberino, Casa Sola, is a rambling villa at the top of a hill on a 300-acre estate of vines and olive trees. Here the very welcoming Gambaro family produces great Chianti Classico Riserva and extra-virgin olive oil. Address: Str. di Cortine, 5, 50021 Barberino Tavarnelle. +39 055 807 5028. Open Daily. NOTE: for groups of 10 people or more, there is also the option of adding a lunch to the visit.http://www.fattoriacasasola.com/en/

If you make the detour to Sant’Appiano, consider visiting Fattoria Sant’Appiano; a one of the oldest Tuscan Farms in the region. The setting also has great views – all the way to San Gimignano. They also produce olive oil, vinegar and spirits. Open from 10:00AM every day. Address: Località S. Appiano, 11, 50021 Sant’Appiano. +39 055 8075541. https://www.santappiano.it/en/

A little further on is I Balzini is a more modern (and a little quirky) winery (est. 1980). It is officially just outside of the Chianti region and features non-traditional varietals such as cabernet sauvignon and merlot with the more traditional sangiovese in a supporting role. They also have olive oil, grappa and jam. Fun! Open from 08:30AM Monday to Friday. Address: Località Pastine, 19, 50021 Barberino Tavarnelle. +39 055 807 5503. https://www.ibalzini.it/en/


The Via Francigena

In medieval times San Gimignano benefited from catering to pilgrims on the Via Francigena – the common name of an ancient road and pilgrimage route running from France to Rome (though some consider it to have its starting point in Canterbury in England).

The route passes through France, Switzerland and Italy. The path was known in Italy as the “Via Francigena” (“the road that comes from France”). In mediaeval times it was an important road and pilgrimage route for those wishing to visit the Holy See and the tombs of the apostles Peter and Paul.

Only a few decades ago, interest in the Via Francigena was limited to scholars. This began to change when people who had travelled the Camino de Santiago (Way of St. James) in France & Spain then wanted to make the pilgrimage to Rome on foot. In Italy, this gave birth to a grassroots organization that began to mark trails and paths. Soon religious and local government agencies joined them in trying to recover the original route. Where possible today’s route follows the ancient one but sometimes it deviates from the historical path in favor of paths and roads with low traffic.

Today walkers and pilgrims follow the route which is now generally well signed. You are likely to notice signs to the Via Francigena as you follow your bike tour route through Tuscany. 1,200 pilgrims were estimated to have walked the route in 2012. Many have also recognized the commercial potential of the route and proprietors have been known to work to divert the path so that it passes around their bar or restaurant!


Useful Contacts en Route

Stores: There is a good supermarket in Barberino – on RHS as you join SR 2. There are also small stores in Ulignano.

Gelato: In our humble opinion, the best gelato in Tuscany can be found in Castellina at Gelateria l’Antica Delizia. If you are riding from Radda, continue through town on the main road (SR 222) towards Siena (you will pass your turn to San Gimignano on RHS). The store is on the LHS of SR 222 (1 KM after the San Gimignano turn) opposite the turn to Castellina Scalo (SP 51). Well worth the detour. Address: Via IV Novembre 47. +39 0577 741 337.

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San Gimignano Loop Rides

Overview

Volterra is the main town to visit today – indeed there are few other towns on this Challenging route. To get there you ride past fields of corn, wheat and sunflowers (in season). You return the way you came but there are also interesting detours. San_Gimignano

The ride starts heading northwest from San Gimignano. After a brief descent out of town, the route climbs up onto a rolling plateau across open arable land. This road is typically quiet and there are few villages.

After the rolling plateau, you join the somewhat busier SP 4 and start a 10 kilometer descent. The descent starts through the trees then the expansive views start as you pass through wide-open fields. You now have clear views of Volterra perched atop its volcanic cliffs to the south. After joining SR 439 you will enjoy some very gentle climbing until the small village of Prato. From Prato, you start paying for all the descending as you climb steeply up to Volterra.

As you climb, you might muse on what DH Lawrence wrote of Volterra (in Etruscan Places – 1932). Lawrence describes Volterra as “somber and chilly alone on her rock … a great bluff of rock that gets all the winds and sees all the world. Volterra is a sort of inland island, still curiously isolated, and grim.” Lawrence was there on a cold, windy afternoon in April 1927, which may explain his bleak outlook, but even in summer the city is still stark and imposing and the windmills on the surrounding hills are testament to the high winds that commonly sweep through the area.

Your route brings you into the city on a narrow, twisting lane – avoiding the busier tourist highways – that is little changed since Lawrence was here. After passing the remains of an Etruscan Necropolis (now little more than a field with bumps), you arrive at Porta Diana. To your right are the ruins of a Roman amphitheater, straight ahead (through the gate) is a medieval lane (Via Guarnacci becoming Via Giacomo Matteotti) that takes you into the heart of this ancient city.

Well before the Romans arrived, Volterra was a thriving Etruscan metropolis (5th century BCE) several times its current size. The Museo Etrusco Guarnacci is well worth a visit if you want to learn more about this ancient past. Alternatively, head to the opposite side of Volterra – along Via Guarnacci, Via Giacomo Matteotti and Via Porta all’Arco – to a well-worn Etruscan gateway and surrounding walls.

 The town is centered on the Piazza dei Priori – a pleasant square surrounded by a palace, a museum and a cathedral – all worth visiting. Entrance to the palace (Palazzo dei Priori) includes a tower with spectacular views of Piazza_dei_Priorithe city’s roofs and the countryside beyond. The palace is one of the oldest civic palaces in Tuscany (1208) and is said to be a model for Florence’s Palazzo Vecchio.

The size and historic integrity (there is little modern development within the city walls) means that one of the best ways to appreciate Volterra is simply to wander the lanes and alleyways. If the central square is busy with tourists, you will soon lose them as you radiate away.

You leave Volterra on the more sweeping SP 15 (better for descending than the route via Prato) before rejoining the route you came in on for the return to San Gimignano.

Route Options

The route described above – and in your turn-by-turn directions – is the Challenge route as the terrain means that there is no Intermediate route available today.

Challenge Route

This is a big day with a very steep climb up to Volterra that includes 11 steep switchbacks! You can mitigate this climb, somewhat, by riding up to Volterra on the slightly busier, but better graded, SP 15.

If you are intent on visiting Volterra, there is really no way to shorten the ride.

If you want a slightly different route back, turn left off SP 15 and head up to Villamagna and through Iano and San Vivaldo before rejoining the described route at Il Castagno. Taking this detour on the way back avoids climbing on SP 15 and SP 4 and is a quieter route with more villages. With this detour adds ten kilometers and 200 meters of climbing.

Easiest Route

For those wanting an easier ride, Certaldo makes a good alternative destination to Volterra. Certaldo may not be as famous or as spectacular as Volterra but with its red-brick towers and stately palaces, the tiny old town (Certaldo Alto) is quite striking. Certaldo was also the home of Giovanni Boccaccio (1313 to 1375). Boccaccio was a true Renaissance man and one of Italy’s most famous medieval writers. You can visit his house in the old town as well as a medieval church and palace. Unfortunately, you need to navigate the large modern town to get to the small old town but the riding is relatively mellow.

To get to Certaldo, head south from San Gimignano on the Ulignano road (SP 127). As the main road turn sharp right, turn left, signed “San Beneditto 6.” At the stop sign turn left onto SP 95, signed “San Beneditto.” When you reach the main road (SP 1) take a left then a right to stay on SP 95 signed “S. Gimignano 12” and “Badia a Elmi 1” respectively. Follow SP 95 to a stop sign where you turn left onto SP 1, signed “Certaldo 1”. After crossing a bridge, take the second exit at the roundabout (straight). At the railway, go under the pedestrian underpass and then tale a right and a left following signs to parking for “Certaldo Alto” and “Funiculare.” Continue straight up this road (Via Dante Alighiere turning into Via Ferruci). Note, there are sections where you will need to walk your bike as the road is pedestrianized or one way the other way. When you get to the end of the road (with an arch in the wall ahead of you), turn left onto Via Roma and then next right onto Via del Castello. This road climbs up to the old town becoming Via Boccaccio (if in doubt, go up). All the main sites are along this road.

Return to San Gimignano the way you came. This route downhill on the way out and uphill on the way back.

Epic Route

On this route, you follow the Challenge ride to Volterra. From Volterra, follow the route marked on the map to Montecatini. From here you are on small lanes as you descend to SR 68. After a few kilometers on SR 68, you head north on the quiet and twisty SP 14 – all the way up to La Sterza. After a few kilometers heading south on SR 439, you are back on small lanes navigating the villages of Fabbrica and Montelopio to reach Villamagna. From Villamagna, continue through to Iano and San Vivaldo before rejoining the described route at Il Castagno. With this option, the total distance is 130 kilometers with an epic 2400 meters of climbing.

Lunch

Depending which ride you are doing, the obvious places for lunch are Volterra or Certaldo.

In Volterra, the volume of tourists means that getting a great meal is not as guaranteed as some other towns in Italy.

For a simple – but good – pizza, we would suggest Dioniso Vegetarian Restaurant. Even if you are a confirmed carnivore, it is probably still the best pizza in town. To get here keep following the curve of Via Guarnacci (the road leading from Porta Diana) as it becomes Via Giacomo Matteotti and then Via Porta all’Arco and the restaurant is on the LHS at Via Porta all’Arco, 15. +39 0588 85371. Open Daily from 11:00AM – 3:00PM. http://www.lifebistrot.com/

For a more substantial meal, Osteria dei Poeti has good Tuscan food and is easy to find – 100 meters past Porta Diana through an archway on RHS as Via Guarnacci becomes Via Giacomo Matteotti (just after you pass Torre Toscana on LHS). Open: 12:00PM – 3:00PM Friday to Wednesday. Closed on Thursdays. Address: Via Giacomo Matteotti, 55. +39 0588 85100. https://osteriadeipoetivolterra.wordpress.com/

In Certaldo Alto, we would recommend Taverna Antica Fonte in the heart of the old town. The food is great, service pleasant and you can see San Gimignano from the airy terrace. What better way to fuel up for the climb back. Open from 12:00PM every day. Address: Via Valdracca, 25, 50052 Certaldo. Turn right down Vicolo dell’Osteria just before reaching the castle. +39 0571 652 225. https://www.tavernaanticafonte.it/

On the longer ride options, most of the villages you pass through have decent (and mostly tourist-free) trattorias.

Wineries en Route

There are no major wineries on today’s route.

Useful Contacts en Route

Stores: There are several supermarkets in Volterra including a large Conad – that stays open over lunchtime – on SP 15 as you ride out of town. Via Pisana, 38. +39 0588 81351.

Most of the villages you pass through on the longer ride options have small store though these typically close from 1:00 PM to 4:00 PM.

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San Gimignano to Sovicille

Overview

Today you transition from hilltop towns to the more open Val di Merse. However, to get to this, flatter terrain, there are some hills to be climbed!

The day starts easily enough, with a two-kilometer decent out of San Gimignano. However, there is then an almost symmetrical climb on the other side of the valley before another long descent. And so, the theme of the day is set: down-up-down. The good news is that there are acres of rolling vineyards (and a high-security prison) to distract you from the climbing.

After a short section through Castel San Gimignano on the busy SR 68, you turn off onto a beautiful, twisting road with very little traffic or habitation. The terrain also changes to be a little drier and more rugged – a mix of olive groves and sheep pastures.

The next town is Casole d’Elsa; a charming yet unassuming village with a regular market and great delicatessen. This is the first lunch option on the route – at about the halfway point. Apart from a museum and a church, there are few “sights” as such but the town square is pleasant and – even if you are not stopping for lunch – it is worth riding through to refill water bottles and pick up a snack.

After Casole, you are back into rolling farmland and enjoying another long descent past arable crops in fields that have been farmed for centuries. Ten kilometers on from Casole you come to the best lunch stop on the route – in the small hamlet of Mensano. The Osteria here has a big reputation and it is well worth a little extra climbing to reach the village. It is also worth the detour to the village for the 12th-century parish church of St John the Baptist (Pieve di San Giovanni Battista) and a truly expansive view from the park at the top of the village – a steep climb and great photo op!

Route Options

The route described above – and in your turn-by-turn directions – is the Challenge. The Intermediate route start partway along this route – see below for the various options.

Challenge Route

None of today’s climbs are too steep but there are five of them. The last climb of the day is 10 kilometers but it is well graded. Much of today’s riding is on quiet backroads but there are isolated villages dotted along the route to provide rest stops.

If you are staying at Relais La Suvera in Pievescola, you do not ride the final ten kilometers to Sovicille. Rather you stop in Pievescola and start the next day with this climb (unless you choose to start with a van transfer).

Intermediate Routes

The only practical way to shorten today’s ride is to ask for a van transfer partway along the route. The transfer options with distance and climbing are shown below:

  • Casole: 30 KM / 720 meters
  • Mensano: 20 KM / 340 meters
  • Pievescola: 15 KM / 280 meters
Epic Route

From San Gimignano head to Volterra. The climb up to Volterra is steep with 11 switchbacks. From Volterra, there is a ten-kilometers descent on the busy SR 68 before you climb up to Pomarance on quiet country roads. From Pomarance, there is a great cross country route via Montecastelli Pisano and Monteguidi. From here you rejoin the regular route, at Mensano – with an early start this makes a good place for lunch. This epic ride is 110 KM with 2150 meters of climbing.

Lunch

The two best-placed towns for lunch are Casole d’Elsa and Mensano. Mensano is a little further along the route and a nicer setting. Pievescola is the last town before the final, 10 kilometer climb.

In Casole: Caffe Casolani is an understated local cafe located on the LHS of the main street – after the main square. The menu (Tuscan of course) varies with the season and the service is relaxed and friendly. There is seating on the street as well as inside. Open: Friday to Wednesday from 8:00AM, closed on Thursdays. Address: Via Casolani, 41. +39 0577 948 734. https://www.caffecasolani.com/

Just after Casole – and a detour off the route – Bar Visconti in Castello di Casole is an elegant and expensive restaurant in an upscale, 5* hotel on a hill. Bar Visconti is their more casual restaurant that also serves pizza. Open from 11:00AM every day. Address: Località Querceto, 53031 Casole d’Elsa. +39 0577 961508. https://www.belmond.com/hotels/europe/italy/tuscany/belmond-castello-di-casole/dining

In Mensano, Osteria del Borgo is a notch up from your typical village osteria with excellent local food in a quaint village. Eating here also gets you a little further along the route before taking your lunch break. Try the fried zucchini flowers! Open from Friday to Wednesday from 12:00PM – 2:30PM. Closed on Thursdays. Address: Via Ricasoli, 25, 53031 Mensano. +39 0577 963911.

There is also a restaurant in Pievescola – on the last climb of the day. Ristorante alla Pieve Enoteca is a husband-and-wife-run trattoria and wine bar. Standard Tuscan fare plus wild boar menu and fish dishes. Open daily from 12:00PM to 2:30PM. Address Via Provinciale, 22-26, 53031 Pievescola. +39 0577 961 028. http://allapieve.it/en/

Wineries en Route

There are no major wineries on today’s route but you will likely see signs along the way to some small establishments.

Useful Contacts en Route

Stores: There is a good but small supermarket on the main square in Casole. There is also a nice delicatessen further down the main street on the RHS.

There is a small store (Alimentari) and a bar next door on the LHS of the main street in Pievescola. Open from 6:00AM every day (closes at 1:00PM on Sundays). Address: Via Provinciale, 43, 53031 Pievescola. NOTE: This store may close over lunchtime.

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Sovicille to Asciano/Casabianca

Overview

On this Intermediate route, you start out relatively flat (flat for Tuscany) across the Val di Merse, then you have a lumpy middle over the Crete Senesi and, finally, a long haul up the hill to Casabianca at the end: something for everyone!

The day starts with an easy spin across the Val di Merse – an open plane that in summer is carpeted with sunflowers. The first 10 kilometers is pleasant if somewhat unremarkable. Once you cross over the SS 223 highway (in a tunnel at this point) things get more scenic – you also get glimpses of the Siena skyline over your left shoulder – as you traverse the open, rolling hills of the Crete Senesi (literally “Sienese clays” for the distinctive grey color of the soil that is sediment from the Pliocene sea which covered this area between 2.5 and 4.5 million years ago).

After Ville di Corsano, the descent down to Monteroni d’Arbia is interrupted by two very-steep-but-thankfully-short climbs and you enter the flat, open Val d’Arbia. Monteroni has little to detain you – though it is a useful place to restock on food and water before heading back to the hills.

After crossing the Arbia River, you start another climb over open countryside. There are no villages before Asciano and the terrain is open and exposed. As you might expect, the views are stunning here as you ride along a ridge with rolling fields of rich, Sienese clay to either side. To the north you see Siena and to the south Monte Amiata; to the west the coastal hills and to the east the ridge of the Apennines. After five-kilometers of climbing, you enjoy a long sweeping descent down to Asciano.

Asciano has ancient roots having been an Etruscan, Roman and Lombardy settlement. Now, however, it is a sleepy town not quite on the tourist routes but still pleasantly welcoming with plenty of facilities. Most things of interest are on the main street through the historic center: Corso Giacomo Matteotti. At the northern end is the Museo d’Arte Sacra with paintings from Sienese master from the 14th and 15th centuries. At the southern end is the Romanesque basilica of Sant’Agata, which you pass as you exit the old town. In the middle is the small, central square of Piazza Giuseppe Garibaldi – a delightful place to sit and watch the world go by. It also has a café, bakery and small deli store.

If you are staying in Casabianca, Asciano is the best place for lunch as you will then have plenty of time for the climb up to Casabianca. The climb from Asciano to Casabianca is over ten kilometers but it is never too steep and there are short sections that are flat and downhill to offer relief. Open views alternate with shady forests as you reel in the final challenge of the day. Casabianca is little more than two dots on a map – one a Hotel (Borgo Casabianca) and
one an agriturismo (Podere Alberese).

Route Options

The route described above – and in your turn-by-turn directions – is the Intermediate Route.

Note that if you are staying in the town of Asciano (not Casabianca) all the routes below will be 10 KM shorter and with 275 meters less climbing.

Intermediate Route

This ride is mostly rolling with no very-long climbs except for the 10-kilometer climb out of Asciano to Casabianca (for those staying in Casabianca). While this climb is reasonably graded, coming at the end of the day, as it does, it can be challenging for less aggressive riders. As a consequence, this Intermediate route is borderline Challenging for those staying at either of the accommodations at Casabianca.

If you are at staying at Relais La Suvera in Pievescola, you start the day by completing the last part of yesterday’s ride from Pievescola to Sovicile – please see the San Gimignano to Sovicille Directions.

Easiest Route

The only practical way to shorten the ride is to ask for a van transfer partway along the route. Of course, all these options still leave you with a relatively long climb from Asciano to Casabianca. The transfer options with distance and climbing are shown below:

  • Ville di Corsano: 37 KM / 690 meters
  • Monteroni: 27 KM / 550 meters
  • Asciano: 10 KM / 300 meters

Casabianca/Asciano to Montalcino

Overview

Today’s Intermediate route has charming villages, a 14th-century abbey and a walled medieval city. The day ends with a 10-Montalcinokilometer climb up through Brunello country to majestic Montalcino.

The riding starts with a pleasant cruise down to Trequanda. This peaceful town is one of the larger villages in the area. The main attraction is the pleasant piazza with a Romanesque church – with its brown checkered façade – as well as a restaurant, a café/bar and the town hall. This is where the townsfolk meet and makes a great spot for a coffee break. If you are minded, the streets off the piazza are nice to wander and some lead to great views across the surrounding countryside.

ChiusureWith a little careful navigation, you leave Trequanda on a steep country road that descends from the town through forests before climbing up through open countryside to the tiny hamlet of Chiusure. The town is small but has a couple of nice places to eat as well as commanding views down to Monte Oliveto Maggiore – the 14th-century abbey that is the next point on your route.

After Chiusure you ride past gullied cliffs of the gray clay that is characteristic of the area. This is the clays that the Crete Senesi (literally “Sienese clays”) is named after and some say it is like the surface of the moon. In fact, the soil is sediment from the Pliocene sea which covered the area between 2.5 and 4.5 million years ago.

After a few kilometers you arrive at the entrance to the abbey of Monte Oliveto Maggiore. To get to the abbey itself, you walk Monte_Oliveto_Maggioreacross a medieval drawbridge and down a brick road through thick woods. The abbey was founded in 1313 by Bernardo Tolomei, a jurist from one of the most prestigious families in Siena. The name comes from the Mount of Olives in the Holy Land. The Abbey’s cloisters and frescos alone make it a great stopping-off point – though note that the abbey buildings are closed over lunchtime.

From the abbey you enjoy a long, rolling descent down to Buonconvento in the Arbia Valley. As you approach Buonconvento, the town looks somewhat unpromising. However, the modern outskirts hide a well-preserved medieval walled village. In times past, this was a defensive outpost for Siena. Now it’s a good place for lunch! BuonconventoThe extensive use of brick is characteristic of Sienese towns and gives the building a warm, soft patina. The main tourist attraction is Museo d’Arte Sacra della Val d’Arbia which includes a Madonna and Child by Matteo Giovanni as well as interesting wood and marble sculptures.

Once you leave the protection of the walls at Buonconvento, you head south and are faced with a steady but well-grade ten-kilometer climb up to Montalcino. The climb ends with a series of sharp switchbacks just outside of Montalcino. While not a major highway, you will be on the Montalcinomain route from Siena and will experience some tourist traffic. There are no villages on the way up but there are a number of wineries to provide nice break points, if needed. Please allow yourself plenty of time for this last section of the ride, stay hydrated, and ride carefully. Generally, the earlier you start this climb the happier your experience!

Route Options

The route described above – and in your turn-by-turn directions – is the Intermediate route.

Intermediate Route

After the initial climb out of Casabianca, the route settles into a mix of rolling and descending with the occasional short-sharp hill. After Buonconvento, however, there is a 10-kilometer climb up to Montalcino with 400 meters of climbing.

Easiest Route

The only practical way to shorten the above ride is to ask for a van transfer partway along the route. Of course, all these options still leave you with a long climb on a relatively busy road up to Montalcino. The transfer options with distance and climbing are shown below:

  • Chiusure: 25 KM / 530 meters,
  • Buonconvento: 14 KM / 450 meters.

The only way to avoid climbing up SP 45 to Montalcino is to get a van transfer all the way to Montalcino and enjoy a loop ride from there: for example, to the Abbey of Sant’Antimo. This option is 20 kilometers with 370 meters of climbing.

Epic Route

This Epic ride, heads south from Trequanda on small country lanes through a string of small villages down to Pienza. From Pienza you continue south across open countryside, through Contignano, in the direction of Radicofani on the SP 96. When you reach the SP 478, you head west (on the SP 18) across the forested shoulder of Monte Amiata via Campiglia d’Orcia before “enjoying” a long slog up to Montalcino past Castelnuovo dell’Abate. This route is 95 kilometers with 2000 meters of climbing.

Lunch

ChiusureThe two places to eat today are either Chiusure or Buonconvento. If you are planning to visit the Abbey of Monte Oliveto Maggiore you may want to consider that the abbey is closed from 12:00PM to 3:15PM when deciding where and when to lunch.

In Chiusure three are a couple of good options in this small and unpretentious village. For the best food, head into the center of the village and eat at Locanda Paradiso. Tucked into a corner of a small, scrappy square, this small, family-run restaurant serves a small selection of classic Tuscan dishes. Nothing too fancy but good value. Open Tuesday to Sunday from 12:30PM – 2:30PM. Closed on Mondays. Address: Via Porta Senese, 25, 53041 Chiusure. +39 0577 707 016.

For the best views, head to the outskirts of the village and eat at the aptly-named Ristorante Le Terrazza. As well as typical Tuscan fare this restaurant also serves pizza – though not always at lunchtime. Address: Via delle Piazze 3 – 53041 Asciano. +39 340 711 3200.

In Buonconvento: head to the old town – along Via Soccini where there are a number of restaurants. Unfortunately, the Buonconventonumber of day trippers means that the food is just good rather than stellar and the prices are similar to the cities rather than the countryside.

La Porta Di Sotto is a pleasant osteria and wine bar (enoteca) that offers a modern take on Italian cuisine. There is outside seating just off the main street. Open: Thursday to Tuesday from 12:00PM – 2:30PM. Closed on Wednesdays. Address: Via Soccini, 76, 53022 Buonconvento. +39 0577 808 386. http://www.laportadisotto.it/

A little further down Via Soccini, the popular Ristorante Da Mario is a more traditional, family-run trattoria with more reasonable prices. There is limited outside seating on the main street as well as a simple dining room inside. Open from 12:00PM – 2:15PM every day. Address: Via Soccini, 60, 53022 Buonconvento. +39 0577 806157.

Wineries en Route

Today you head into Brunello country – one of Italy’s most prestigious wines. There are numerous opportunities to stop for a tasting to help break up the climb up to Montalcino.

Il Paradiso di Frassina (or Mozart’s Winery) has been inhabited since at least 1,000 AD but what makes it more unusual is that they play music to their vines – in particular Mozart. The vineyard is researching how sound waves can beneficially affect the vines; a project supported by the Universities of both Florence and Pisa. Unfortunately, the winery is up a steep gravel track so not practical for road bikes but worth listening for as you pass! On RHS SP 45 as you climb up to Montalcino. Open Monday to Friday from 10:00 AM to 5:00 PM. Tours are also available on Saturday mornings by request only. Address: Località Frassina, 41, 53024 Montalcino. +39 0577 839 031. https://www.alparadisodifrassina.it/

 Cantina di Montalcino is a starkly modern structure that might look more at home in Napa than Tuscany. It has been the only Cantina_di_Montalcinocooperative winery in the area for more than 40 years and includes 100 small farms. To save energy, 50% of the winery is located underground and most of their electric energy is provided by solar cells. On LHS as you climb up SP 45 to Montalcino. Open Monday to Saturday, 8:30 AM to 6:00 PM. Address: Loc. Val Di Cava, 53024 Montalcino. +39 0577 848704. https://www.cantinadimontalcino.it/en/

A little further up SP 45 (also on LHS), Val di Suga is the Tenimenti Angelini group’s wine estate in Montalcino and another producer of the prestigious Brunello di Montalcino. The property extends over an area of 120 hectares, 55 of which are planted in Sangiovese vines. Open daily from 11:00 AM to 6:00 PM. Address: Localita Val di Cava, 53024 Montalcino. +39 0577 804101. https://valdisuga.it/en

On the LHS of SP 45, located with the reception of the hotel of the same name, Canalicchio di Sotto estate is a small producer of renowned Brunello – though having started in 1978 they are one of the newer wineries. Like many wineries, they also produce excellent olive oil. Address: Località Canalicchio di Sotto, 8, 53024 Montalcino. +39 0577 848 476. http://www.lambardimontalcino.it/web/

Alternatively, once you have arrived in Montalcino, there are numerous wine bars that will gladly supply a tasting of a whole range of the local wines. One of the best is Enoteca di Piazza Montalcino. With over 100 wines to choose from this is a great way to taste a range of Brunellos (and other wines such as Rosso di Montalcino, Nobile di Montepulciano, and Chianti Classico) without scouring the countryside. The staff is knowledgeable and friendly. They can also arrange shipping back to US. They have some seating out on the street but the real thing happens in the cool wine room. Open: 9:00AM – 7:00PM every day. Located close to the center of town, address: Piazza Giuseppe Garibaldi, 4, 53024 Montalcino. +39 0577 849 194. https://www.enotecadipiazza.com/

Or walk to Il Palazzone – a winery on the outskirts of town. The winery is run by husband and wife team Laura and Marco, who will help you both “taste and understand” Brunello. Their motto is, “We drink what we can and sell the rest.” From the end of the ride, take the 3rd exit on the roundabout (staying on SP 14) then immediately take a right turn on Via del Poggiolo; after the pharmacy. The winery is about 300 meters down this lane that turns to dirt after passing the cemetery on LHS. Address: Località le Due Porte, 245, 53024 Montalcino. +39 0577 846142. Open Mon to Fri but given the distance, it might be worth calling ahead if you plan to visit. http://www.ilpalazzone.com/en

Useful Contacts en Route

Stores: There are small stores in both Trequanda and Chiusure.

The biggest supermarket on the route is in Buonconvento, on the LHS as you ride into town – the Coop at Via Don Milani, 4, 53022 Buonconvento. +39 0577 809103.

Note that none of these stores are open between 1:00 PM and 3:30 PM.

Museums: In Buonconvento: – Museo d’Arte Sacra della Val d’Arbia at Via Soccini, 17. + 39 0577 807 181. Open Tuesday to Sunday, 10:00AM to 1:00PM and 3:00PM to 6:00PM.

Sights: Abbazia di San Galgano is open 9:00AM – 5:30PM every day. Address: Strada Comunale di S. Galgano, 53012 Chiusdino. +39 0577 756 738. https://abbazia-san-galgano.business.site/

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Montalcino Loop Rides

Overview

San_QuiricoIf you rode up to Montalcino yesterday, you will know that any ride today will involve some climbing. The Challenge route today has some long climbs but there are some shorter options too – or just spend today relaxing and enjoying the commanding views, the restaurants, cafés, churches and museums in this restful town.

The Challenge route heads east down the hill towards Torrenieri. The ride down is on a relatively busy road, but you are traveling downhill so it is not too long before you are through this small town and back on quiet roads and climbing up towards San Quirico. San Quirico is a very pleasant, rambling town with 15th-century walls and a Romanesque church. As such it makes an excellent coffee (or early lunch) stop. Your route through town takes you past the 12th-century Collegiata dei Santi Quirico e Giulitta. This pretty church is well worth a stop – it is architecturally interesting and nice and cool after the climb up to San Quirico.

After riding through San Quirico, you enjoy a five-kilometer descent to the turn-off to Bagno Vignoni. It is well worth the ½-kilometer detour to this renaissance spa town. Do not be put off by the shabby, modern approach road. Walk past the Hotel Le Terme and you discover a tiny hamlet at the center of which is an arcaded Renaissance pool fed by bubbling hot springs. There are also ruins of an old mill – Parco dei Mulini – nearby with fine views of La Rocca: the next target on your journey.Bagno_Vignoni

From Bagno Vignoni you start climbing through more rugged countryside and Monte Amiata dominates the southern horizon – though its top is often shrouded in cloud. Straight ahead of you is La Rocca – a precipitous and scrappy fort built in the 1200s on a limestone outcrop. The nearby town of Castiglione offers a good stopping point to catch your breath after the climb with its cobbled streets and three medieval churches.

There is nothing to mark the highpoint of the ride – shortly after Castiglione – other than a view that looks like you should be able to see to Rome! You also start a 10-kilometer descent to the railway station of Monte Amiata Scalo. In between, the road twists through rugged countryside with few villages. Confusingly, Monte Amiata Scalo is the low-point of the ride and also the name of the highest mountain in southern Tuscany.

From Monte Amiata Scalo, the only way is up … for nearly 15 kilometers – the first four kilometers of which are steep. Thankfully, after the first part of this climb you arrive at a good rest point at one of Tuscany’s most charming abbeys: the Abbey of Sant’Antimo. The Abbey – a short detour from the town of Castelnuovo dell’Abate – is a former Benedictine monastery said to have been founded by Charlemagne in the 700s. Disused for over 500 years, the abbey is now maintained by a small community of Cistercian monks: the Premonstratensian Canons. The isolated setting of the remaining 12-century church makes this one of the most picturesque religious sites in Tuscany. If you are lucky you will hear the monks singing a Gregorian chant. [You can also hike to the Abbey from Montalcino, if you are having a day off the bike – see Route Options see below.]

MontalcinoFrom Castelnuovo dell’Abate you still have another 9 kilometers of climbing but there is another – more secular – beak point for those that want it. Fattoria dei Barbi is both a rustic tavern as well as one of the oldest and most respected producers of Brunello wines.

Your ride ends, at the top of the hill, in Montalcino.

Route Options

The route described above – and in your turn-by-turn directions – is the Challenge Route. The Intermediate route takes you partway along this route – see below for the various options.

Challenge Route

This is a hill ride with 475 meters of climbing in the last 13 kilometers – from the station of Monte Amiata Scalo.

If you are staying at Castello di Velona you first ride up the hill (SP 55) to Montalcino to join the start of the ride. If you are staying at Canalicchio di Sopra, you ride a couple of kilometers up SP 45 to join the route at SP 14.

Intermediate Route

The easiest way to shorten the Challenge ride, above, is to turn around in San Quirico and ride back the way you came. While this reduces the distance to 32 kilometers there is still 720 meters of climbing much of which is on the busy SP 14 back up to Montalcino.

Easiest Route

A better option for a short ride is to ride directly to the Abbey of Sant’Antimo. With this option, you can visit one of Tuscany’s cultural gems without riding the full, 50-kilometer, circuit. Rather you ride 20 kilometers with 330 meters of climbing. There are also a couple of nice wine-tasting options along this ride.Abbey_Sant'Antimo

The nearby town of Castelnuovo dell’Abate has options for lunch or visit Fattoria dei Barbi on the way back for excellent Brunello and lunch in their taverna. Also, great for lunch, and closer to the main road, is Osteria La Crocina on the RHS, just after the Fattoria dei Barbi turn on the way back up to Montalcino.

If you are staying at Castello di Velona, a visit to the Abbey of Sant’Antimo also makes a great short ride option. It is just a few kilometers from this hotel, up SP 55, to the abbey. You could then choose to continue up SP 55 to Montalcino (and/or Fattoria dei Barbi) for a slightly longer ride.

Epic Route

This route explores the slopes of Monte Amiata. At over 1700 meters this is southern Tuscany’s highest mountain complete with ski resort, radio masts and a large cross.

From Montalcino, you take the SP55 south and head across to Vivo d’Orcia. From here, circle around via Pescina and climb up on small forested roads following signs to Vetta Amiata. Near the top there is a cluster of hotels and small bars. From here it is a short walk to a stunning viewpoint with a large cross in the shape of the Eifel Tower. An in-and-out ride to the summit of Monte Amiata – via Castelnuovo dell’Abate and Vivo d’Orcia – is 100 kilometers with 3000 feet of climbing.Pescina

If you loop back via Abbadia San Salvatore the ride is almost the same distance and you get to visit this interesting town (though you do have to fight your way through some modern sprawl to get to the old town [Centro Storico]) and confusingly, the 11th-century abbey is in newer part of town.

If you are riding this epic route, we recommend using a GPS unit or loading the GPS files onto a smart phone.

Alternative Activities

For a restful day: Montalcino is a great place to have a rest from cycling – if that is what you want. The town itself is small but there are plenty of things to do – the Towns and Cities section of this guidebook.

For an active rest from cycling: you can hike down to the 12th-century abbey of Sant’Antimo – see above. The walk (signed #2h) takes around 3-hours. We strongly recommend getting directions from the tourist office in Montalcino if you plan to make this walk.

To get to the start of the walk: from the roundabout where the bike ride starts, walk up SP 14, signed to Grosseto, and, almost immediately, take a right turn after the pharmacy down Via del Poggiolo. There is a walking map on the signpost on your LHS at the start of this road. As the road becomes a track, after the cemetery, keep straight following #2 signs. You walk through fields and woodland via the hamlet of Villa a Tolli. After a rugged downhill hike, you come to the Abbey – isolated in beautiful countryside. From the Abbey, it is another 15 minutes to reach the village of Castelnuovo dell’Abate. There are a couple of buses each afternoon from Castelnuovo dell’Abate back to Montalcino. We recommend checking with the tourist office for the exact times. The route number is P1 (Monte Amiata Scalo to Montalcino).

Lunch

Where you lunch will depend largely on the route you choose.Bagno_Vignoni

On the way to Castelnuovo dell’Abate: Osteria La Crocina is just 3 kilometers down the hill from Montalcino on the way down to Castelnuovo dell’Abate. Traditional organic Tuscan food with some nice additions such as salt cod and octopus. One of the nicest restaurants in the area with exceptional food in a nice, relaxed country setting. Open: 12:30PM – 2:0PM from Thursday to Sunday, closed Monday to Wednesday. Address Località La Crocina, 1, 53024 Montalcino. +39 0577 847197. http://www.agriturismopiombaia.it/

The Taverna dei Barbi is located at the esteemed winery of Fattoria dei Barbi – see below. The wine is outstanding, though the food is merely good. However, if you take the wine tasting and food in combination, it is worth the excursion off the route. Open: 12:00PM – 7:00PM Thursday to Tuesday. Closed on Wednesdays. Address: Localita Podernovi, 170, 53024 Montalcino. +39 0577 847143. http://www.fattoriadeibarbi.it/en/hospitality/taverna-dei-barbi/

In Castelnuovo dell’Abate: the traditional choice is Osteria Bassomondo – set back from the main intersection. The usual Tuscan fare competently prepared in plain surroundings. Open: 9:00AM – 8:00Pm Tuesday to Sunday. Closed on Mondays. Address: Via Bassomondo, 7, 53024 Castelnuovo dell’Abate. + 39 0577 835619.

A little more modern – with an outdoor terrace – is Locanda Sant’Antimo on the opposite side of SP 55 at Via Bassomondo, 8. + 39 0577 835 615

In Castiglione d’Orcia: La Cisterna nel Borgo is worth the detour up the hill for innovative cooking, great service and a lovely setting. Turn right off the main route just after entering Castiglione, signed to Rocca d’Orcia. After entering Rocca, continue straight up the hill past the Zona Traffico Limitado sign. The restaurant is towards the top of the hill; on the LHS in a small square with a well. Open from 12:0PM to 2:00PM Tuesday to Sunday. Address: Borgo Maestro, 37, 53023 Rocca D’orcia, Castiglion d’Orcia. +39 0577 887280. http://www.cisternanelborgo.com/

On the route itself, Osteria Bassomondo is a good alternative. Open: 9:00AM – 8:00PM Tuesday to Sunday. Closed on Mondays. Address: Via Bassomondo, 1, 53024 Castelnuovo dell’Abate. +39 0577 835619. https://www.ristoranteosteriabassomondo.it/

In Bagno Vignoni most of the restaurants suffer from too many tourists and not enough locals so the food is often just OK (by local standards) and relatively expensive. However, what they lack in food they make up for in setting.

One of the best located – on the central square/pool – is La Terrazza. Open 12:30PM – 2:30PM every day. Address: Piazza delle Sorgenti, 13, 53027 Bagno Vignoni. +39 0577 887157. http://www.laterrazza-bagnovignoni.it/it/index.html

You can also find a nice sandwich or bruschetta at La Bottega di Cacio. It has a small but pleasant outside seating area. Located next door to Osteria Leone just to the south of the main square – turn left as you walk into the hamlet. Open: 11:00AM – 7:00PM from Wednesday to Monday. Closed on Tuesdays. Address: Piazza del Moretto, 31, 53027 Bagno Vignoni. +39 0577.887477.

In San Quirico there are many good options for lunch. Ristorante Da Ciacco is close to the top of the list with great food creatively prepared and pleasant service. Located on the main route through town. Open: 12:30PM – 2:00PM from Wednesday to Monday. Closed on Tuesdays. Address: Via Dante Alighieri, 30A, 53027 San Quirico d’Orcia. +39 0577 897312. https://daciacco.business.site/

The nearby Osteria Del Cardinale also has great local food. Open: 11:00AM – 10:00PM Tuesday to Sunday. Closed on Mondays. Address:  Via Dante Alighieri, 35A, 53027 San Quirico d’Orcia. +39 0577 899 945. Closed Monday. http://www.osteriadelcardinale.it/?lang=en

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Montalcino to Montepulciano

Overview

It is in the nature of hilltop towns that when you leave them you go down. Today is no exception as you head down from Abbey_Sant'AntimoMontalcino and head across the Orcia valley towards Montepulciano – another hilltop town.

Today’s Challenge ride starts out heading south with nine 9 kilometers of descending to one of Tuscany’s most beautifully located abbeys: the Abbey of Sant’Antimo. The Abbey – a short detour from the town of Castelnuovo dell’Abate – is a former Benedictine monastery said to have been founded by Charlemagne in the 700s on the site of a Roman villa. Disused for over 500 years, the abbey is now maintained by a small community of Cistercian monks: the Premonstratensian Canons. The isolated setting of the remaining 12th-century church makes this one of the most picturesque religious sites in Tuscany. If you are lucky you will hear the monks singing a Gregorian chant; they have a hymn session seven times a day.

After Castelnuovo dell’Abate, you continue the descent for a further four kilometers to the confusingly-named Monte Amiata; confusing because it is also the name southern Tuscany’s highest mountain. In fact, Monte Amiata is a mountain that dominates the horizon for much of the day – though it is often shrouded in cloud. The town (and railway station) of Monte Amiata is the lowest point on today’s ride. A fact you will “appreciate” as you enjoy the rugged and isolated 400-meter climb from here to Castiglione.

The cobbled streets and three medieval churches of Castiglione’s old town make this a pleasant rest stop. If you have the legs, the 10th-century fortress of Rocca d’Orcia is also worth a visit. Castiglione is also the first feasible lunch-stop on the route but most people choose to press on to get further along the route before stopping for food.

After another four kilometers of descending, you reach the turn-off to Bagno Vignoni. It is well worth the ½-kilometer detour to this renaissance village. Do not be put off by the shabby, modern approach road. Walk past the Hotel Le Terme and you discover a tiny hamlet at the center of which is an arcaded Renaissance pool fed by bubbling hot springs. There are also ruins of an old mill – Parco dei Mulini – nearby with fine views of La Rocca: where you have just ridden from. Bagno Vignoni is a good lunch option or pickup point if this is your last day.

After a short section on the busy SR 2, you head east, following the route of the Orcia River before heading north toward Monticchiello. As you leave the river, you begin climbing again – on tree-lined lanes that roll over open Tuscan farmland.

Monticchiello makes a perfect, if distant, lunch stop. This fortified medieval village is basically one large, well-preserved castle. From the walls of the village there are stunning views south across the Val d’Orcia to Monte Amiata (the mountain not the railway station!). Best of all, one of our favorite restaurants in the area is built into the castle walls with a terrace that perfectly frames the expansive views.

If this is your last day, consider asking to be met by your guide here. It really is a great spot! If not, it is back on the bike for Montepulcianoanother 200 meters of climbing up to Montepulciano. One reward for the post-lunch exertion is that you ride up a series of cypress-lined switchbacks that look like they are straight out of a travel brochure. Soon after the summit of the climb you have views across to Lake Trasimeno in Umbria.

Surprisingly, you enjoy a rolling descent into the “hilltop” town of Montepulciano. However, after all that climbing, even the small rises can cause aching legs to complain.

Route Options

The route described above – and in your turn-by-turn directions – is the Challenge Route. The Intermediate route start partway along this route – see below for the various options.

Challenge Route

Most of the climbing on this route is in two long slogs of almost 10 kilometers each. The first of which, from Monte Amiata Scalo, is through open, exposed, and remote countryside.

Intermediate Routes

The only practical way to shorten today’s ride is to ask for a van transfer partway along the route – assuming this is not your last day. The transfer options with distance and climbing are shown below. All these options still leave you with some climbing to do up to Montepulciano.

  • Monticchiello: 10 KM / 250 meters (have a late start and a transfer to lunch)
  • Pienza: 15 KM / 200 meters (visit Pienza then ride to Montepulciano on the busy SS 146)
  • Pienza: 20 KM / 450 meters (visit Pienza before joining the described route via Monticchiello)
  • Bagno Vignoni: 25 KM / 480 meters
  • Castiglione: 30 KM / 490 meters (start with a five-kilometer descent)

If this is your last day, you could shorten the ride by asking for an alternate pickup point. The pickup options with distance and climbing are shown below.

  • The Abbey of Sant’Antimo: 10 KM / 75 meters (visit the abbey and have lunch in Castelnuovo dell’Abate before being collected)
  • Castiglione: 25 KM / 550 meters (with lunch at Rocca)
  • Bagno Vignoni: 30 KM / 550 meters (end with lunch or soaking in a thermal pool)
  • Monticchiello: 40 KM / 780 meters (lunch on the terrace overlooking the Valley)
Epic Route

This Epic ride follows the Challenge ride for 20 kilometers out of Montalcino. Then you turn right onto SP 18/d and take a scenic route via the hilltop village of Campiglia to Radicofani. Like Rocca in Castiglione, Radicofani is one of the most imposing fortresses towns in Tuscany. Under the protection of the fortress is a pretty town of the same name and a Capuchin convent. It’s also a good lunch stop. From Radicofani, it’s a “relatively” benign cruise into Montepulciano past acres of rolling farmland – except, that is, for the climb up past Monticchiello.

Epic+ Route

You can add an ascent up Monte Amiata to the Epic ride above – as well as an extra 35 kilometers and 1,000 meters of climbing – and turn it into a stage of the Giro d’Italia. At over 1700 meters, Monte Amiata is southern Tuscany’s highest mountain complete with ski resort, radio masts, and a large cross.

From Montalcino, you take the SP55 south and head across to Vivo d’Orcia. From here, circle around via Pescina and climb up on small forested roads following signs to Vetta Amiata. Near the top there is a cluster of hotels and small bars. From here it is a short walk to a stunning viewpoint with a large cross in the shape of the Eifel Tower. From the top, you continue the ride via Abbadia San Salvatore and onto Radicofani to rejoin the ride above.

If you are riding this epic route, we recommend using a GPS unit or loading the GPS files onto a smart phone. Before attempting an ascent of Monte Amiata, it is worth checking whether the summit is in cloud. Easily done as the mountain can be seen from much of the ride down from Montalcino.

Lunch

Where you lunch will depend largely on where you plan to start and end your ride as well as how many miles you want under your belt before relaxing.

In Castiglione d’Orcia: La Cisterna nel Borgo is worth the detour up the hill for innovative cooking, great service and a lovely setting. Turn left off the main route just before leaving Castiglione signed to Rocca d’Orcia. After entering Rocca, continue Castiglione_d'Orciastraight up the hill past the Zona Traffico Limitado sign. The restaurant is towards the top of the hill; on the LHS in a small square with a well. Open from 12:00PM to 2:00PM Tuesday to Sunday. Address: Borgo Maestro, 37, 53023 Rocca D’orcia, Castiglion d’Orcia. +39 0577 887280. http://www.cisternanelborgo.com/

On the route itself, Osteria Bassomondo is a good alternative. Open: 9:00AM – 8:00PM Tuesday to Sunday. Closed on Mondays. Address: Via Bassomondo, 1, 53024 Castelnuovo dell’Abate. +39 0577 835619.

In Bagno Vignoni most of the restaurants suffer from too many tourists and not enough locals so the food is often just OK (by local standards) and relatively expensive. However, what they lack in food they make up for in setting.

One of the best located – on the central square/pool – is La Terrazza. Open 12:30PM – 2:30PM every day. Address: Piazza delle Sorgenti, 13, 53027 Bagno Vignoni. +39 0577 887157. http://www.laterrazza-bagnovignoni.it/it/index.html

You can also find a nice sandwich or bruschetta at La Bottega di Cacio. It has a small but pleasant outside seating area. Located next door to Osteria Leone just to the south of the main square – turn left as you walk into the hamlet. Open: 11:00AM – 7:00PM from Wednesday to Monday. Closed on Tuesdays. Address: Piazza del Moretto, 31, 53027 Bagno Vignoni. +39 0577.887477. http://labottegadicacio.com/

In Monticchiello: one of our favorite lunch spots for today is Osteria La Porta. On the left, just inside the gate of this medieval fortress-city, this restaurant has both great food, pleasant service and a view that will live with you for months. Open: 9:00AM – 11:00PM every day. Address: Via del Piano, 1, 53026 Monticchiello. +39 0578 755 163. https://www.osterialaporta.it/it/index.html

MonticchielloAs a strong backup, Ristorante Daria serves traditional and more modern dishes in a restored building but with a modern interior in the heart of the town. Not quite as good as La Porta but has improved massively over the last couple of years and it is more reasonably priced and good to have if La Porta is full. Open: 12:30PM – 2:30PM Thursday to Tuesday. Closed on Wednesdays. Address: Via S. Luigi, 3, 53026 Monticchiello. +39 0578 755170. https://www.ristorantedaria.it/en/

In Radicofani: there are a couple of reasonable choices. Trattoria le Ginestre is a popular restaurant on the road into town. Open Friday to Wednesday from 12:00PM – 3:00PM, closed on Thursdays. Address: Via Odoardo Luchini, 18, 53040 Radicofani. +39 0578 55918.

La Grotta is in the heart of the old town on Piazza Sant’Agata. They serve good-value local food in basic surroundings. Open: 12:00PM – 2:30PM from Wednesday to Monday. Closed on Tuesdays. Address: Via della Piazzetta, 1-13, 53040 Radicofani. +39 0578 55866.

Wineries en Route

If you are only doing a short ride down to the Abbey of Sant’Antimo, it would be practical to visit wineries in the Montalcino area. For example, on the road down to the Abbey, Fattoria dei Barbi offers a full-on Brunello experience. The Colombini family has lived in the area since 1352 and has owned this estate since 1790 – so they have staying power. They also have great wine. Open: 11:00AM – 6:00PM every day. Tours weekdays at noon and 3. Down a small lane off SP 55, halfway to Castelnuovo dell’Abate. Address: Loc. Podernovi, 170, 53024 Montalcino. +39 0577 841 111. http://www.fattoriadeibarbi.it/

Shortly before Montepulciano, Cantina Ercolani has an informal tasting room with wine, olive oil and many other local products. The wine is respectable and the atmosphere is pleasantly informal. Look for the hand-written signs on RHS of SS 146 just after making the turn from SP 88. Open: 9:00AM – 10:00PM every day. Address: Via di Gracciano nel Corso, 82, 53045, Montepulciano. +39 0578 716764. https://www.ercolanimontepulciano.it/?lang=en

Alternatively, there are plenty of places to taste in Montepulciano.

Useful Contacts en Route

Stores: There are several small stores in both Castiglione and Bagno Vignoni. Apart from that, it is a little sparse so we suggest stocking up where you can.

In Castiglione. At the ERG gas station, turn left off the main road following signs to “inCoop.” Via della Rocca, 15. +39 0577 887 481.

In Bagno Vignoni La Bottega di Cacio is a charming store with pleasant outside seating area. Piazza del Moretto +39 0577.887477. Closed Tuesdays.

Sights: Abbey of Sant’Antimo. Hymn service seven times a day. Open daily from 6:45 AM to 9:00 PM. Address: Localita’ S. Antimo, 222, 53024 Castelnuovo dell’Abate. +39 075 678 9754. https://www.antimo.it

Hot Springs: Piscina Val di Sole is the public hot springs in Bagno Vignoni. The large panoramic swimming pool is fed by the thermal water of Bagno Vignoni and has great views of the Val d’Orcia. Owned by Hotel Posta Marcucci but open to non-guests. A day pass is €27.00. Open 9:30AM – 6:00PM every day. Turn left at the roundabout just outside the old square and follow signs. Address: Via Ara Urcea, 43, 53027 Bagno Vignoni. +39 0577 887 112. https://www.postamarcucci.it/

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Montepulciano Loop Rides

Overview

Today’s Intermediate ride is an out-and-back to Pienza – on the UNESCO World Heritage List. To get there you descend across Montepulcianorolling fields into the Val d’Orcia. Pienza is also renowned for its Pecorino sheep’s-milk cheese, which dominates the menus of many of the restaurants in town.

Your ride starts heading south with a short climb on the relatively busy SS 146. However, you are soon on quiet lanes in the Val d’Orcia with picture-postcard-perfect views of large rolling hills and cypress-lined driveways. In spring the fields are bright green, in summer they are full of golden wheat, and in fall the rich ochre clay is exposed by deep ploughing. At any time of year, it lifts the spirits to ride across this terrain.

Halfway down the decent you pass the charming castle-town of Monticchiello. If you didn’t visit yesterday, it is well worth the small detour (either on the way out or the way back). The town also has an exceptional restaurant.

A couple more kilometers of descending sets you up nicely for the five kilometers of climbing up to Pienza. The large open fields let you see your target from the beginning of the climb. The road zigzags around a series of switchbacks as you reel yourself in towards the iconic profile of this 15th-century city.

It is well worth allowing yourself plenty of time to explore Pienza. The town was conceived by Pope Pius II as a “new town” that would showcase all the best Renaissance humanist concepts of town-planning. It was built on the site of the Pope’s birthplace and it was intended to “relieve the extreme misery of its inhabitants.” Construction started in 1459 and many of the main buildings were finished just three years later.

Piazza_Pio_IIThe Piazza Pio II and the buildings around it (the Piccolomini Palace, the Borgia Palace and the cathedral) are noteworthy and good to visit if you have the time and energy. Alternatively, the town lends itself to aimless meandering. Nothing is more than two blocks from the central street – Corso Il Rossellino. Your ride ends at the start of this pedestrian street and the Piazza Pio II is halfway along it. There are also a number of nice restaurants in the old town with surprisingly good food, considering the popularity of the destination.

The walkway around the city walls – on the south side of the city – offers great views of both the Val d’Orcia as well as of the city and its iconic cathedral tower. Take your bikes for a picture of you riding down the lane (Via del Casello). Perfect for a make-your-friends-jealous Facebook posting! To get there, turn right down one of the whimsically-named lanes after the main square (Piazza Pio II): Via del Bacio, Via dell’Amore, Via della Fortuna and Via del Buia (known collectively as the streets of love).

You can leave the town through the tiny gate at the eastern end of the Corso Il Rossellino (and turn right onto SP 18) or return to the small park at the western end of the street where the ride directions start.

You ride back the way you came; though the different time of day and reversed perspective make it feel very different.

Route Options

The route described above – and in your turn-by-turn directions – is the Intermediate route.

Intermediate Route

Most of the climbing on this ride is in two stretches: one five-kilometer climb up to Pienza and an eight-kilometer climb past Monticchiello as you head back to Montepulciano.

To shorten this ride, we would suggest riding to Monticchiello for lunch. This reduces the mileage and climbing to 20 kilometers and 470 meters respectively.

You could also ride to Pienza along the ridge on SS 146. However, this is a relatively busy road and still includes a reasonable amount of climbing. With this option, the distance is 25 kilometers and the climbing is 370 meters.

Easiest Route

For a very short ride around town, ride along a small lane around the walls of the city. This route includes the imposing church of San Biagio (Chiesa di San Biagio) as well is some surprisingly rural lanes. The ride starts at the southwestern end of town at the same intersection as the main ride but you head north on a small tree-lined lane (Viale della Rimembranza), signed “Relais San Bruno” and “Chiesa di San Biagio.” Just before the church, turn left to go around the church. Then follow this paved lane (Via dei Canneti) as it meanders past vineyards and fields. Pass under two arches just before the end of the road and turn right at the stop sign onto Viale Mario Mancattelli. At the end of this street, turn right onto Via Elio Bernabei. The ride ends at the top of the hill at the northeaster end of the old town.

Challenge Route

This Challenge ride heads south to Radicofani – a quiet medieval town with one of the most imposing forts in Tuscany. After lunch in Radicofani, you head back via the pleasant village of Contignano. This route will take you miles from the standard tourist runs as you cross rolling farmland.

Epic Route

This Epic ride follows the above Challenge ride but continues past Radicofani through San Casciano dei Bagni, and on to Trevinano. The destination is not that remarkable in an area filled with beautiful villages. This ride is more about the journey – through forests, across farmland and past multiple small villages. You also get bragging rights to say that you have cycled all the way through Tuscany and into Lazio.

San Casciano dei Bagni also makes a good lunch spot and good turnaround location for this ride.

Alternative Activities

For a more relaxing alternative, you might choose to spend the day in Montepulciano. This car-free town is perfect for strolling. Many cafés have terraces with fantastic views across the valley and beyond into Umbria. And, there is no shortage of interesting sights: palaces, churches, piazzas and a cathedral.

Lunch

Depending on your chosen route, good places for lunch include Monticchiello, Pienza, Radicofani and Trevinano.

In Monticchiello: one of our favorite lunch spots for today is Osteria La Porta. On the left, just inside the gate of this medieval fortress-city, this restaurant has both great food, pleasant service and a view that will live with you for months. Open: 9:00AM – 11:00PM every day. Address: Via del Piano, 1, 53026 Monticchiello. +39 0578 755 163. https://www.osterialaporta.it/it/index.html

As a strong backup, Ristorante Daria serves traditional and more modern dishes in a restored building but with a modern interior in the heart of the town. Not quite as good as La Porta but has improved massively over the last couple of years and it is more reasonably priced and good to have if La Porta is full. Open: 12:30PM – 2:30PM Thursday to Tuesday. Closed on Wednesdays. Address: Via S. Luigi, 3, 53026 Monticchiello. +39 0578 755170. https://www.ristorantedaria.it/en/

In Pienza you are spoiled for choice. This is also the home of Pecorino cheese, so expect to see it feature in many menus.Pienza

For sheer impact, you cannot beat La Terrazza del Chiostro. Crisp linen cloths adorn tables that cluster on a terrace replete with great views. The food isn’t too bad either – though this is a destination restaurant so you will be lunching with fellow tourists and not locals with prices set accordingly. The only danger is that you won’t want to leave to ride back. On the RHS of the main street as you walk into town. Open: 12:15PM – 2:45PM every day. Address: Corso il Rossellino, 26, 53026 Pienza. +39 0578 748183. https://www.laterrazzadelchiostro.it/

You will see more locals at Trattoria La Buca delle Fate. The restaurant is located in an austere palace dating back – like most things on this street – to the 15th-century. Good local restaurant, at the higher end for food (and price) though service can be a little slow. No outdoor seating. Past the main square on the RHS of the main street. Open: 12:30PM – 2:30PM Tuesday to Sunday. Closed on Mondays. Address: Corso Rossellino, 38, A, 53026 Pienza. +39 0578 748 448. http://www.labucadellefate.com/it/index.php#welcome

To see pecorino cheese dominate a menu, head to Osteria Sette Di Vino. Who could fault grilled cheese and bacon for less than €10! However, the setting of this restaurant is the best reason to recommend it as it is located on a very pleasant square. To get there turn left down a small alley off man Piazza (Piazza Pio II) as you walk into town. Open: 12:00PM – 2:00PM Thursday to Tuesday. Closed on Wednesdays. Address:  Piazza di Spagna, 1, 53026 Pienza. +39 0578 749 092.

In Radicofani: there are a couple of reasonable choices. Trattoria le Ginestre is a popular restaurant on the road into town. Open Friday to Wednesday from 12:00PM – 3:00PM, closed on Thursdays. Address: Via Odoardo Luchini, 18, 53040 Radicofani. +39 0578 55918.

La Grotta is in the heart of the old town on Piazza Sant’Agata. They serve good-value local food in basic surroundings. Open: 12:00PM – 2:30PM from Wednesday to Monday. Closed on Tuesdays. Address: Via della Piazzetta, 1-13, 53040 Radicofani. +39 0578 55866.

In Trevinano: there is not too much choice in this town. Ristorante La Parolina is a real local’s restaurant – not many tourists make it to town – located in a small house on the main road through town (SP 51). Open: 12:30PM – 2:30PM Wednesday to Sunday. Closed Monday & Tuesday. Address: Via Giacomo Leopardi, 1, 01021 Trevinano. +39 0763 717130. https://www.laparolina.it/

In San Casciano dei Bagni: Ristorante Daniela has better than average food with outside seating and nice views. Located in the castle walls – on the road to the center of town. Open: 12:00PM – 3:00PM every day. Address: Piazza Giacomo Matteotti, 6, 53040 San Casciano dei Bagni. +39 0578 58234. https://www.settequerce.it/en/restaurant-daniela/

Wineries en Route

There are so many wine bars doing tastings in Montepulciano that it makes little sense to ride for your tasting. The exception might be Cantina Ercolani as it is close to the end of your ride. This informal tasting room has wine, olive oil and many other local products. The wine is good and the atmosphere is pleasantly informal. Look for the hand-written signs on RHS of SS 146 just after making the turn from SP 88 on the return to Montepulciano. Open: 9:00AM – 10:00PM every day. Address: Via di Gracciano nel Corso, 82, 53045, Montepulciano. +39 0578 716764. https://www.ercolanimontepulciano.it/?lang=en

Useful Contacts en Route

Stores: There are several small stores in both Pienza and Radicofani. In Pienza, the Coop is on SS146, in the LHS heading towards Montepulciano. It does not typically close for lunch. Address: Via S. Gregorio, 13. + 39 0578 748 582.

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Safety and Enjoyment

Your safety is our first priority and should be yours, too! Here, we share some ideas on helping you get the most from your cycling tour – safely and while having fun.

Riding Safely

We have a few simple rules we ask you to follow:

    1. Always wear a cycle helmet fastened securely while cycling.
    2. Do not ride at night or in the dim light of dawn or dusk.
    3. Ride in single file and with the direction of traffic.
    4. Carry identification, details of your medical/travel insurance and emergency contact details.
    5. Sign an accident waiver indicating you are fit to ride and understand the risks.
    6. All cyclists under 16 years of age:
      • Must wear a florescent safety triangle or high visibility clothing.
      • Need to be accompanied by an adult over the age of 21 who is responsible for their safety at all times while cycling.

Daily Bike Checks

Your rental bikes are checked and tuned before every trip.  However, it is useful to do some regular checks just to keep things running smoothly. These checks should take less than five minutes to do.  Of course, if you’re in any doubt or have any concerns, give us a call and we’ll have a guide come out to you.  If they can’t fix a problem they’ll arrange for a new bike.

Brakes: 

  • Do both brake levers engage the brakes smoothly?  This test is best performed first on a stationary bike and then on a moving bike.
  • Are the shoes spaced evenly on either side of the wheel and the brake blocks close to but not rubbing on the wheel rims?
  • Are cables OK – not frayed – and under tension?

Handlebars & stem:

  • Check alignment – does the wheel point forward when the handlebars point forward?
  • Holding front wheel between legs check for lateral movement when flexing/twisting handlebars.
  • With front brake engaged, move bike back and forth to check for any rocking.  If there is movement, the headset may need tightening.

Gear changing.  This check is easily done as you set out at the start of your ride:

  • Check all front gears engage/change smoothly
  • Check all rear gears engage/change smoothly
  • Are cables OK – not frayed?

Chain:

  • If you’ve been riding in rain or on wet roads, you may want to wipe off your chain and apply a little lube the night before.  In the morning, run a clean rag over the chain to remove any excess oil.
  • But don’t overdo it; an over-oiled chain just attracts dirt.

Wheels & tires:

  • Inflate front & back tires to recommended tire pressure which should be written on the side.
  • Check front & rear wheels spin smoothly with little friction or noise and are true (no wobbles).
  • Check there are no loose or broken spokes in either wheel.
  • Check tires including sidewalls for cuts or other damage.
  • Check tires for any foreign bodies embedded in the tires and remove / replace tires as needed.
  • Are the quick-release mechanisms secure, correctly engaged and pointing backwards?

Frame:

  • Check for cracks and alignment in the frame, the headset & the handlebars – especially if you accidentally dropped the bike.
  • Pay extra attention and feel for problems in carbon forks and carbon rear stays where fitted.
  • General check for any loose parts.

Riding Safely

Here are our favorite top tips to help you have a safe trip.

  1. Ride predictably in smooth lines and avoid weaving or wobbling. When you stop – for example to check your map – we recommend that you move off the road. The more people there are in your group, the more important this becomes.
  2. Stay alert, be aware and anticipate; anticipate what other vehicles will do, anticipate what gear you will need to be in after you stop and anticipate the approaching road surface – do you need to avoid gravel, potholes or broken glass? Should you dismount to cross railroad tracks?  [FACT: 50% of urban accidents happen solo.  That is, people just fall off of their own accord.  A little anticipation would work wonders here.]
  3. Be as visible as you can be. Our fluorescent triangles are available to all guests and we recommend that riders of all standards wear them.  [When riding with our florescent triangles, we have noticed that cars give us a noticeably wider berth as they pass by.]
  4. Choose a safe riding position on the road. Stay as close as is safe to the right-hand side of the road as possible but do not be cowed into a dangerous riding position.  For example, avoid riding on grit, or dangerously broken pavement or where you are at risk of being hit by an opening car door.
  5. Obey the law. Drivers will give cyclist more respect, and you are far safer, if you obey all the traffic laws – including stopping at stop signs, riding on the right-hand side of the road and not riding under the influence of alcohol.  [FACT: 10% of ‘cyclist at fault’ accidents are caused by cyclist using the wrong side of the road.]
  6. Ride assertively but defensively. At intersections, make eye contact with drivers.  Assertive riding is easier for drivers to predict, but cars are bigger and harder than we are, so we always try to avoid getting into confrontations with them.  [FACT: 63% of cyclist collisions occur at intersections.  The most common cause of accidents, where the driver is at fault, is the driver’s failure to yield the right of way.]
  7. Check out your bike and make sure you are confident that it is roadworthy. Everyday check brakes, tires, quick release mechanisms, pedals and headsets.  Everything should fit snuggly and move smoothly.  Whether you are riding your own or a rented bike, the roadworthiness of that bike is your responsibility.

7 Habits of Highly Effective Cyclists

[Apologies to Stephen Covey]

As well as having a safe tour, we are keen for you to enjoy cycling and achieve a real sense of accomplishment.  This is likely to include riding within your limits and not exhausting yourself before lunch.  Here are some thoughts on how to stay happy on your bike.

  1. Eat before you are hungry. Even moderate cycling burns around 300 calories per hour so eat plenty of snacks such as power bars or trail mix.  We need to eat in enough time to allow our bodies to process the food and get the fuel to our legs before the fuel gauge reaches on empty.  Recovering from a fuel deficit is very difficult and will leave you tired for the rest of the day.  So, indulge yourself.  [Everybody’s metabolism is different, but when riding extended distances, it is typical to need to eat something every 45 minutes.  A nice big bowl of pasta the night before and a carbohydrate rich breakfast in the morning also help.]
  2. Drink before you are thirsty. It can get very hot on the bike in this area.  As you sweat, you will lose both water and essential salts.  You will not notice the effects until it is too late.  Drink plenty of water before you start to ride and then take regular sips en route.  [A good target is to drink either water or a sports drink at least every 30 minutes.]
  3. Ride at a pace that feels comfortable. Even when climbing hills, it is good practice to be able to keep a conversation going without being out of breath.  This means changing down to a low gear, keeping your cadence high and taking things easy.  If you are a slow rider riding with fitter friends, have them ride at your pace rather than you struggling to keep up with them.  This will also help them avoid sore legs the next day.
  4. The sun can get very intense, especially in the middle of the day so keep your shirt on and use a high factor sunscreen. [Watch for being burned through the gaps in your cycle helmet.  Many of the best helmets have extra wide gaps for better ventilation.  A bandana under the helmet can make all the difference.]
  5. Relax and change your hand position regularly. This helps avoid shoulder cricks or back aches.  Drop handlebars are better for being able to do this than straight handlebars.
  6. Check your bike. A sticking brake or skipping gear stops you relaxing and can be dangerous.  If you are unsure, talk to your guide, who will be happy to help you check things out if you have a concern.
  7. Smile, you are on vacation!

Seat Height Adjustment

Seat height adjustment is more craft than science.  The most important thing is that you feel safe and confident on the bike.  However, getting your saddle to the right height will also help you stay comfortable on longer rides, avoid saddle sores and conserve your energy while you pedal.

Bike fitters can spend hours getting your fit just right, but here are some simple rules of thumb.

  1. Stand and hold or prop yourself up against a wall.
  2. Position the pedals so the pedal cranks are vertical (one pedals at 12 o’clock and one pedal at 6 o’clock).
  3. Get on your bike and place your feet on the pedals. Move your foot so that your heel is on the pedal at 6 o’clock.
  4. When your seat is at the correct height, your leg (of the foot at 6 o’clock) should be straight but your knee shouldn’t be locked (technically, there should be a 25-30-degree flexion in the knee when the pedal is at the bottom most point).

If your seat is too low, it will make it harder to pedal and you may get knee pain at the front of the knee.  Too high and your hips will go from side to side which will make you tend to ride in too high a gear and you may develop pain at the back of your knees.

Saddle Sores

Saddle sores are the great unmentioned subject of cycling.  However, if you have not been riding much recently and start doing a lot of miles on a bike, you may well become just a little too familiar with this phenomenon.

To prevent sores, it’s helpful to know what they are.  Definition: A saddle sore is a skin ailment on the buttocks due to, or exacerbated by, riding on a bicycle saddle.  It often develops in three stages: skin abrasion, folliculitis (inflammation of the hair follicles) and, finally, abscess.  If it’s not obvious from the definition, it is better to stop the sores in the early stages than try and treat it in the final stage.

The best cure of all is to not get them in the first place.  The best way not to get them is to gradually build up your riding mileage and get used to your bike seat.  Doing rides before you come on the trip will help with this.  Other good preventative measures include:

  • Reducing the friction due to bobbing or swinging motion while pedaling, by setting the appropriate saddle height – see above.
  • If you have a favorite saddle, bring it along and we’ll fit it to your rental bike.
  • Wearing good cycling shorts, with a high-quality chamois insert.
  • Use petroleum jelly, chamois cream or lubricating gel on the chamois to further reduce friction.
  • Do not sit around in damp bike shorts after your ride and thoroughly wash and dry the affected area.
  • A friend who guides extreme mountain biking trips in the Colorado Rockies swears by putting hemorrhoid cream on the affected area. If all else fails, it’s worth a try!

There are pharmacies in all the main towns you’ll stay in if you need medical treatment.  Our primary message would be, if you think you have them, don’t ignore them.

Fixing a Flat

Of course, we hope you won’t ever need this skill – but just in case here is a checklist for fixing a flat – or repairing a puncture in your tyre as the English would say!  If it seems as though there are a lot of steps, you may be reassured by the fact we have seen all these steps completed in just over a minute

Remove the wheel. Sounds simple, but a couple of hints might make this easier.

  • If it’s the rear wheel, first put the chain on the smallest cog. This makes it easier to remove and replace the wheel.
  • Undo the quick release.
  • If it’s the front wheel, you will need to unscrew the quick release a little to get it over the lips on the fork – they’re known as lawyers’ lips!
  • You may have to loosen the brakes a little to get the tire past the brake blocks if there is still some air in the tires. On hybrid bikes this usually means squeezing the brake calipers together and unhitching the cable.  On road bikes there is usually a release mechanism on the caliper itself (or on the brake lever).
  • For the back wheel, you may need to ease back the derailleur a little before the wheel just drops out under gravity.

Let the air out of the tire.

  • For Presta valves, loosen the small nut at the top of the valve and press down.
  • For Schrader valves (like the valves on car tires) press the tip of a tool or stick onto the valve tip.

Before doing anything else, spin the wheel to see if you can find out what caused the flat. If you find it, either remove it now or mark it so you can remove it when you remove the tire.

If you’re very lucky, you’ll now be able to ease the tire off the rim with your bare hands. But to do this you may well need bear’s hands. Alternatively, you’ll need to use tire levers (irons):

  1. Insert the curved end of two tire levers under the edge of the tire about two spokes apart.
  2. Lever back the first tire lever to take the tire off the rim being careful not to pinch the inner tube and so add an extra hole to patch! Hook the free end of the lever around a spoke.  This leaves your hands free to lever back the second tire lever.
  3. Keeping the hooked lever stationary work the other lever around the tire until one side of the tire is completely removed from the rim but leaving the other side still seated on the rim. If a tire is very tight, you may need to engage a third lever.  When the third is in place, the middle one can be removed and re-inserted farther over.
  4. Remove the valve stem of the inner tube first then pull the rest of the inner tube from the tire. Try to keep the inner tube oriented with the tire so that when you find the hole you can navigate back to the same point in the tire and double check that what caused the flat isn’t still embedded.
  5. Look over the external and inside of the tire for damage and embedded debris. Remove any objects.  Then run your finger around the inside of the tire (carefully!) to detect any glass or thorns.  As a final check, inflate the tube and locate the puncture hole.  Check the tire at the corresponding place to ensure the offending object has been removed.  If you skip this step or are just a bit sloppy you may have another flat five minutes after getting back on your bike!
  6. Hopefully, you have a spare tube that your nice tour company gave you at the start of your ride. If not you’ll need to repair the hole in the old tube using a patch kit.
  7. Place some air in the new (or repaired) tube – just enough to give it some shape. Insert the valve stem on the tube into the valve hole in the wheel and then ease the rest of the tube into the tire.  Then ease the tire wall so the tube is sitting in line with the wheel not hanging outside of the wheel.

Now the tricky part.  Starting at the valve, work the tire back onto the rim using your thumbs or the muscle in the palm just under the thumb (actually the abductor pollicis brevis though knowing this won’t help you get the tire back on).  If the last section is hard to get on, try these things:

  • Ensure that the tire that is inside of the wheel is sitting well into the rim.
  • Hold the wheel horizontally against your stomach with the section of wheel without the tire on furthest away from you. Then use your abductor pollicis brevises to roll the tire onto the rim.
  • If none of this helps, use tire levers to work the bead onto the rim. However, if you resort to this there is a real risk of pinching the inner tube and creating another hole and being back to Step 4 above!

Inflate the tire.

As you inflate ensure that the tire is sitting evenly in the wheel.  If not, let out a little wire and reseat the tire in the rim.

When inflated, spin the wheel to ensure there are no bulges or wobbles. If there are, deflate the tire, reseat the tire on the rim and re-inflate.

Replace the wheel. (This is pretty much the reverse of Step 1.)

  • If you didn’t need to loosen the brakes to get the deflated wheel off, you may find you need to do it now to get it back on. A tap with the palm of your hand can also do the trick to ease the tire past the brake blocks.  DON’T FORGET TO RETIGHTEN THE BRAKES BEFORE HEADING OFF!
  • If it’s the front wheel, you will need to retighten the quick release a little after getting it over the fork lips before reengaging the quick release. The pressure needed to close the quick release should be enough to leave a small mark on the palm of your hand but not so much you need to apply all your strength and all the strength of your cycling partner to close it.
  • For the back wheel, you may need to ease back the derailleur a little before the wheel drops into place.

My Customized Itinerary

If you’ve made it this far, there’s likely an Oregon cycling trip in your future. We’d love to create the perfect custom itinerary for you! Please submit your request below for a no-obligation personalized cycling vacation to be created for you.

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