Tuscany, Italy

Picture Perfect

Tuscany, Italy

Picture Perfect

Tuscany, Italy

Picture Perfect

Tuscany, Italy

Picture Perfect

Tuscany, Italy

Picture Perfect

Scroll down for details

Highlights

  • Custom itineraries and uniquely personal service
  • Ride from one medieval hilltop town to the next
  • Cycle along cypress-lined lanes in the Val d’Orcia – so picture-perfect it is a World Heritage Site
  • Experience 1,000 year old olive groves
  • At the end of the day, savor delicious Tuscan food and wine

Seasons

Spring, Summer, and Fall

Starting / Ending City

Siena or Florence, Italy

Tour Length

3 to 14 days

Trip Types

◊ Self-Guided
With our Self-Guided tours an expert local guide takes care of your transfers, route briefing, luggage moves, and planned transfers. They are also available should you need mechanical assistance, help with a dinner reservation, or general questions. You have a GPS unit, maps, and a detailed guidebook to help you select your route, choose where you eat, and, generally, explore the area.

◊ Guided Group
Our Guided tours allow your group to explore a destination with an expert local guide with a dedicated support vehicle. You will also have GPS units, maps and a detailed guidebook to help learn about both the major sights and the hidden gems. Your guide takes care of both you and all the logistics – from route advice to bottle washing.

Request Itinerary
Private Tuscany Italy Cycling Tours

    X

    d Design Your Tour

    Tell us about your perfect tour so that we can customize an itinerary.

    Filter Region ▼
    • All Regions
    • North America
    • Europe
    Hawaii's Big Island
    Hawaii
    Oregon
    Oregon
    San Juan Islands
    San Juan Islands
    Provence, France
    France
    Catalonia, Spain
    Catalonia, Spain
    France's Pyrenees
    France
    Holland
    Holland
    Southwest Ireland
    Ireland Coast
    Puglia, Italy
    Italy
    Tuscany, Italy
    Italy
    Douro Valley, Portugal
    Portugal
    Istrian Peninsula, Croatia
    Portugal

    Where do you want to stay?

    Budget

    Two Star Silverton Inn Suites

    Simple B&Bs and more modest hotels but all well-kept with en suite facilities

    z Select

    Classic

    Four Star accommodation

    Smaller hotels or luxurious B&Bs with very personal service often including wine tasting

    z Select

    Luxury

    Luxury accommodation

    Some of the nicest full-service hotels in the area. Typically include a pool and a good restaurant

    z Select

    When, how many days and how many in your party?

    Let us know when you would like to travel, how long you would like your tour to be and how many people might be in your party.

    Next

    What else should we know?

    Tell us more about you and what you're interested in! While completely optional, providing us with more information helps us design the perfect tour for you.

    Next

    Where should we send your custom itinerary?

    Thank you for providing us with your tour preferences. The next step will be for us to contact you with a prepared itinerary which we can further customize. We will be in touch soon!

    Thank you for your submission. We will be in contact very soon!

    Y

    Sample Itinerary

    Tuscany Italy cover photo

    Our Tuscan bike tours are about simple pleasures perfectly executed. Like Tuscan cuisine,we use only the very best ingredients: vineyards, olive groves, and a visible history that dates back to before the Roman Empire. Highlights include medieval hilltop towns (San Gimignano, Montalcino and Montepulciano), the World Heritage Site of Val d’Orcia, and the forested lanes of the Chianti wine region. And, at the end of the day, quite exceptional food and wine. Most people also take the opportunity to visit Siena and Florence during theirstay either of which can be the start and/or end cities for this tour.

    TOUR LENGTH

    6 Days / 5 Nights

    ACCOMMODATION OPTIONS

    Budget  

    Classic  

    Luxury  

    START & END

    Siena

    SERVICE HIGHLIGHTS

    • Private transfer from Siena with bike set up and full route briefing at the start of your tour
    • Bilingual guides delivering superior service
    • Handpicked accommodations with breakfast
    • On-call roadside assistance
    • Luggage moved between lodgings and optional participant transfers along the routes
    • GPS units, maps, directions and a comprehensive guidebook

    OPTIONAL EXTRAS

    • Alternative start and/or end location in Florence or Florence Airport
    • Cooking classes
    • Wine tours
    • Customize your route

    BIKE AVAILABILITY

    DAY-BY-DAY FLOW

    Day 1: Siena to Radda

    Day 2: Radda Loop Day

    Day 3: Radda to San Gimignano

    Day 4: San Gimignano to Sovicille

    Day 5: Sovicille to Montalcino

    Day 6: Montalcino Loop day

    a

    Day One - Siena to Radda in Chianti

    The Intermediate ride starts with a van transfer to Castelnuovo Berardenga. From here, you ride across rolling farmland with majestic views of the medieval city of Siena. Centuries-old farmhouses pepper a landscape that has been farmed since before the Roman Empire. En route, you pass Castello di Brolio that dates back to the 12th century and was the birthplace of the iconic Chianti wine. It is still one of the best wineries in Italy. From Brolio, the road climbs gently up to the walled medieval village of Radda.

    Leisure riders will be transferred to Castello di Brolio where you join the Intermediate route described above.

    Challenge riders start out on the Intermediate route but take the hilly route to Radda via Lecchi – a one-street village nestled in the folds of the Tuscan hills that has a great lunchtime restaurant.

    The Epic ride heads north from Castelnuovo Berardenga and climbs steadily on remote roads for 10 miles up to Monteluco before descending back into the valley to join the Challenge ride at Lecchi.

    Castello di Brolio dates back to the 12th century and was the birthplace of the iconic Chianti wine

    Siena to Radda in Chianti Italy cycling tour segment visits Castello di Brolio and more

     

    RIDE OPTIONS

    Leisure
    15 miles with 1,000 feet of climbing

    Intermediate
    25 miles with 2,300 feet

    Challenge
    25 miles with 2,600 feet

    Epic
    30 miles with 3,400 feet

    OVERNIGHT TOWN

    Radda in Chianti

    Radda is in the heart of the Chianti Region and was founded by the Etruscan (pre-Roman) civilization. Its network of narrow streets (closed to traffic) is tightly enclosed within stunning 14th-century walls. This walled gem appears little-changed since medieval times.

    a

    Day Two - Radda Loops

    Today’s Intermediate ride heads east to Badia Coltibuono – a beautifully-located 11th-century abbey that is now a winery, a restaurant, and a great stop for lunch. From the abbey, you enjoy a fast, twisting descent into Gaiole – a classic Chianti market town nestled in a steep-sided valley alongside a fast-flowing river. After gelato in the town square, you climb back up to Radda through the beautiful one-street village of Lecchi and past the exceptional Castello di Ama winery.

    Leisure riders follow the start of the Intermediate route but take an easier route back from Gaiole (past a famous artisan’s ceramics workshop).

    Challenge riders head north up to the market town of Greve. En route, you pass the most famous butcher shop in the country (in Panzano) as well as the lovely village of Montefioralle with two Romanesque churches and two great restaurants. The return ride is on quiet roads through dense forests.

    Today’s Epic ride follows the Challenge ride out of Radda but continues north of Greve to Strada in Chianti. The return route south is along one of the most stunning ridge rides in the whole of Tuscany.

    Eat lunch at Badia Coltibuono – a beautifully-located 11th-century abbey that is now a winery and restaurant

    Radda Italy cycling tour Loops

    RIDE OPTIONS

    Leisure
    15 miles with 1,600 feet of climbing

    Intermediate
    20 miles with 2,200 feet

    Challenge
    30 miles with 4,400 feet

    Epic
    45 miles with 5,000 feet

    OVERNIGHT TOWN

    Radda in Chianti

    Radda is in the heart of the Chianti Region and was founded by the Etruscan (pre-Roman) civilization. Its network of narrow streets (closed to traffic) is tightly enclosed within stunning 14th-century walls. This walled gem appears little-changed since medieval times.

    a

    Day Three - Radda to San Gimignano

    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 hills.

    The Intermediate ride (which includes some Challenging climbing) takes you along a forested ridge to Castellina: a well-preserved hilltop town with one of the best gelato stores in Tuscany. You then descend into the Elsa Valley before “enjoying” a long climb up to the towers of San Gimignano.

    The Leisure ride joins the above route at Barberino – a pretty town with several good restaurants.

    Today’s Epic ride is similar in character to the Intermediate route (quiet road and stunning views) but it heads much further north to San Casciano before looping down to San Gimignano via Castelfiorentino. Except for 6 miles of respite around Castelfiorentino, you are always either climbing or descending on this ride – in places, quite steeply.

    Transition from rural Radda to imposing San Gimignano

    Radda to San Gimignano Italy cycling tour segment

    RIDE OPTIONS

    Leisure
    15 miles with 1,200 feet of climbing

    Intermediate
    30 miles with 2,800 feet

    Epic
    55 miles with 4,600 feet

    OVERNIGHT TOWN

    San Gimignano

    This stunning medieval hilltop town sits imposingly in the folds of large rolling hills. In medieval times great towers were built to boast of the importance of feuding nobles. To this day, the town still impresses as you ride up to it. Inside the town, a Romanesque cathedral and a 12th-century palace complete the splendor.

    a

    Day Four - San Gimignano to Sovicille

    Today’s Challenge ride starts with a mile-long descent passing acres of rolling vineyards. At the bottom of the descent, the terrain becomes more rugged – a mix of olive groves and sheep pastures. En route, you can visit an artisanal farm specializing in Pecorino cheese made from raw sheep’s milk. Your lunchtime destination is either Casole d’Elsa or Mensano (further along the route). Both are charming and unassuming villages and both have good restaurants. Casole also has a regular market. From Casole on, the landscape is tamer with many beautifully rural villages along the route. You will also start to see vast fields of sunflowers. Again, you are riding on little-trafficked roads that twist and turn through the folds of the hills.

    Intermediate riders will take a van transfer to Casole to join the Challenge ride described above.

    Leisure riders will take a van transfer to Mensano, which leaves one well-graded climb to Sovicille.

    Today’s Epic route is a challenging loop via Volterra and Pomarance along some beautiful, small roads with challenging climbs.

    Beautifully rural villages and fields of sunflowers

    San Gimignano to Sovicille Italy cycling tour segment

     

    RIDE OPTIONS

    Leisure
    15 miles with 1,100 feet of climbing

    Intermediate
    20 miles with 1,900 feet

    Challenge
    35 miles with 3,750 feet

    Epic
    70 miles with 7,100 feet

    OVERNIGHT TOWN

    Sovicille

    Though little-visited by tourists, Sovicille has its own quiet charm with a pleasant and well-preserved center that can trace its roots back to 1000 CE. It has a Roman mosaic and has been variously ruled by the Florentines, the Sienese, the Medici family and the French. Most guests stay just outside of Sovicille, in the tiny hamlet of Toiano.

    a

    Day Five - Sovicille to Montalcino

    The Challenge ride starts relatively flat as you roll past acre after acre of sunflowers. You then head west into an area called Crete Senesi (literally “Sienese clays”). The area gets its name from the distinctive, ocher-colored, clay that dominates the plowed fields here. Your ride takes you to Murlo – a tiny ring of houses that form a fortified village, which has been faithfully restored. Shortly after Murlo, Buonconvento (“Happy Place”) makes for a good lunch stop. The town has a perfect, walled medieval village at its center. From here it is a steady climb past vineyards to the archetypal hilltop town of Montalcino.

    Intermediate riders will be transferred to Murlo and join the Challenge ride described above.

    Leisure riders will take a van transfer to Buonconvento.

    Epic riders head south from Sovicille into the Colline Metallifere (“Metal-bearing Hills”). The jewel in these little-traveled hills is San Galgano – the ruined abbey here is among the greatest gothic buildings in Italy.

    The breathtaking Val d’Orcia is an area so iconic of Tuscany that it is a UNESCO World Heritage Site

    Sovicille to Montalcino Italy cycling tour segment visits Val d’Orcia, a UNESCO World Heritage Site

     

    RIDE OPTIONS

    Leisure
    10 miles with 1,000 feet of climbing

    Intermediate
    15 miles with 1,900 feet

    Challenge
    35 miles with 3,700 feet

    Epic
    65 miles with 8,500 feet

    OVERNIGHT TOWN

    Montalcino

    Montalcino is little-changed since the 16th century. The car- free center is a delightful maze of narrow streets and pleasant plazas. Through every archway you get glimpses of the surrounding countryside. It is also home to the esteemed Brunello di Montalcino – one of Italy’s best red wines.

    a

    Day Six - Montalcino Loops - Last Day

    If you rode up to Montalcino yesterday, you may want to spend today relaxing and enjoying the commanding views, the restaurants, cafés, churches and museums in this restful town. For a change from cycling, you could hike down to the 12th- century abbey of Sant’Antimo. Its famed Gregorian chanting, as well as its rural setting, make it one of the most evocative abbeys in Tuscany.

    Those wanting a Leisure ride will cycle down to the abbey of Sant’Antimo for lunch.

    Intermediate riders will do an in-and-out ride to the town of San Quirico. It is a pleasant ride to this peaceful, rambling town that is surrounded by 15th- century walls.

    Challenge riders will continue beyond San Quirico to Bagno Vignoni. In the center of this tiny hamlet is an arcaded Renaissance pool fed by bubbling hot springs.

    Whatever you choose to do, afterwards, you will be met by your guide for your end-of-tour transfer.

    Ride or walk to the 12th-century abbey of Sant’Antimo, famed for its Gregorian chantingMontalcino Italy cycling tour Loops visits the Sant’Antimo abbey and more

    RIDE OPTIONS

    Leisure
    10 miles with 1,000 feet of climbing

    Intermediate
    20 miles with 2,400 feet

    Challenge
    35 miles with 3,700 feet

    OVERNIGHT TOWN

    None

    As this is the last day of your tour, there is no overnight accommodation unless explicitly requested on booking.

    Radda in Chianti:

    Bottega di Giovannino

    This inn is charming and the owners treat you like family – which here is a good thing! Rooms are simple, clean and most have good views. As a bonus, the inn’s restaurant is one of the most authentic places to eat in town.

    San Gimignano:

    Hotel Leon Bianco

    Situated on the Piazza della Cisterna in the heart of the old town, this family-run hotel could not be better located for exploring this ancient city. Rooms are cozy and clean and many have original features such as exposed wooden beams. Note that rooms facing the square can be noisy during the day and early evening.

    Sovicille:

    Relais Borgo di Toiano – Standard Room

    This hotel is in a wonderful location, in a tiny village in beautiful countryside. Rooms are clean, spacious and tastefully furnished. The staff is very friendly and helpful. The outdoor pool has great views across the tranquil valley – as does the terrace where breakfast is served. We book standard rooms in this category.

    Montalcino:

    SI Montalcino Hotel

    This recently renovated hotel is less than a mile outside of the medieval walls along a country lane. The hotel is perched on the side of a hill with fantastic views across to the hilltop towns of Pienza and San Quirico. Rooms are clean, comfortable and modern. The property includes a pool and a restaurant.

    Tuscany Italy budget hotel features

    ACCOMMODATION NOTES

    Properties in our Budget category are typically simpler B&Bs and more modest inns or hotels. However, all the properties are well-kept with en suite facilities.

    Mix & Match
    You can choose accommodation in different categories in different towns. Please ask for prices.

    Tips & Notes
    Casolare Le Terre Rosse is four miles south of San Gimignano but has a restaurant on the property and a free shuttle into town.
    Relais Borgo di Toiano is two miles northwest of Sovicille. The property has a bar service and offers simple dinners by prior arrangement. Alternatively, there is a restaurant- pizzeria 15 minutes’ walk away.

    Radda di Chianti:

    Palazzo Leopoldo

    A beautifully restored palace just off the central square in Radda. You are literally stumbling distance to several excellent restaurants and bars. The views from the breakfast terrace are spectacular – as are the views from the rooms at the rear of the hotel. Service is friendly and there is a small indoor pool in the basement of the hotel.

    San Gimignano:

    L’Antico Pozzo

    This converted 17th-century convent, within the walls of the city, oozes rustic charm. The name means “ancient well” (which can be visited in the medieval basement). Rooms are simple and airy – some have frescoes. An excellent breakfast is served on an attractive outdoor terrace.

    Sovicille:

    Relais Borgo di Toiano – Superior Room

    This hotel is in a wonderful location, in a tiny village in beautiful countryside. Rooms are clean, spacious and tastefully furnished. The staff is very friendly and helpful. The outdoor pool has great views across the tranquil valley – as does the terrace where breakfast is served. We book superior rooms when available.

    Montalcino:

    Hotel Dei Capitani

    On the edge of the historic old town, this hotel is perfectly situated for exploring Montalcino. The hotel also has panoramic terraces and a small swimming pool. The rooms are small, comfortable and tastefully furnished. Many of the rooms also have nice views across the surrounding countryside.

    Tuscany Italy classic hotel features

    ACCOMMODATION NOTES

    Properties in the Classic category are typically smaller hotels or luxurious B&Bs with very personal service sometimes including wine tasting or evening hors d’oeuvres.

    Mix & Match
    You can choose accommodation in different categories in different towns. Please ask for prices.

    Tips & Notes
    Relais Borgo di Toiano is two miles northwest of Sovicille. The property has a bar service and offers simple dinners by prior arrangement. Alternatively, there is a restaurant- pizzeria 15 minutes’ walk away.

    Radda in Chianti:

    Il Borgo di Vèscine
    This 13th-century hamlet has been converted into a luxury resort. Set in glorious isolation among the vineyards, the cottages of the village have been renovated into charming guest rooms. The property has a winery and an outdoor pool with expansive views across the valley. We book suites when available.

    San Gimignano:

    Hotel La Collegiata
    This converted 16th-century monastery is now a luxury hotel set in peaceful gardens. Both the conversion to a hotel and the décor are very tasteful and there are amazing views back to San Gimignano. This is the perfect place to relax and escape the tourist bustle of the town. We book rooms facing San Gimignano when available

    Sovicille:

    Relais Borgo di Toiano – Suite

    This hotel is in a wonderful location, in a tiny village in beautiful countryside. Rooms are clean, spacious and tastefully furnished. The staff is very friendly and helpful. The outdoor pool has great views across the tranquil valley – as does the terrace where breakfast is served. We book junior suites when available.

    Montalcino:

    Castello di Velona

    This resort, spa and winery sits at the end of a ridge above a bend in the Orcia River. Based around a military fortress that dates back to the 11th century, the hotel is an exercise in refined ambience and modern comforts. All the rooms face the breathtaking landscape of the Val d’Orcia.

    Sovicille – Upgrade:

    Castello di Casole

    Belmond Castello di Casole is truly exceptional hotel located in the rolling hills of rural Tuscany. The hotel is housed within an ancient castle and surrounded by sprawling vineyards. The property is one of the largest private land holdings in Italy. There are two excellent restaurants, spa, pools and more. A unique blend of storied past with modern indulgence.

    Tuscany Italy luxury hotel features

    ACCOMMODATION NOTES

    Properties in our Luxury category are some of the nicest full-service hotels in the area. They typically include spa facilities and a good restaurant.

    Mix & Match
    You can choose accommodation in different categories in different towns. Please ask for prices.

    Tips & Notes
    Il Borgo di Vèscine is four miles west of Radda but has an excellent restaurant on the property.
    Hotel La Collegiata is one and a half miles north of San Gimignano but has an excellent restaurant on the property.
    There are limited hotel options in Sovicille. For this reason, Relais Borgo di Toiano is more modest than the other hotels in this category. See next page for an upgrade option.
    Relais Borgo di Toiano is two miles northwest of Sovicille. The property has a bar service and offers simple dinners by prior arrangement. Alternatively, there is a restaurant- pizzeria 15 minutes’ walk away.
    Castello di Velona is seven miles beyond (south of) Montalcino but has an excellent restaurant and beautiful spa on the property.

    A hotel upgrade is available in Sovicille to the Castello di Casole for $1,780 per room per night. See description opposite.

    Note that the Castello di Casole is 6 miles from Casole d’Elsa and 15 miles from Sovicille. Guests staying here have a shorter ride from San Gimignano. Guests riding to Asciano or Montalcino typically choose to take a van transfer to Sovicille at the start of that day.

    BIKE CHOICES

    Hybrids bikes, a cross between a mountain bike and a road bike

    Hybrids bikes are a cross between a mountain bike and a road bike. They have a relaxed riding position and are great for beginners and intermediate riders. A typical model is the Trek 7.3 FX with Shimano components and high-pressure road tires for better cycling efficiency than your typical hybrid.

    Road bikes, a racing style bike with drop handlebars

    Our road bikes are a racing style bike with drop handlebars. The road bikes are faster bikes than the hybrids with less upright riding position. A typical model is the Émonda ALR 5 with aluminum frame, carbon forks, and Shimano 105 components. (NOTE: Some of the smaller roads in Puglia can be a little rough making a hybrid bikes a better choice for some riders.)

    eBikes, designed to give you a little extra assistance when climbing hills

    Our eBikes are designed to give you a little extra assistance when climbing hills. The ride position is very similar to our hybrids. We typically rent Scott E-Sub equipped with a 250W E-drive Bosch motor. If one rider in a couple is stronger than the other, an eBike can be a great choice for the less-strong rider.

    Your Own Bike, if you have a favorite bike, we can help you get it to your destination as well as set it up once it is there

    If you have a favorite bike, we can help you get it to your destination as well as set it up once it is there. Please ask about options for bike shipping and assembly.

    group of cyclists

    OPTIONAL EXTRAS

    Receiving & Assembly
    per bike charge to receive bike from shipper, assemble the bike and repack it and deliver it to a shipper at the end of the tour.

    Bike Boxes 
    a per box charge for the extra logistics needed to handle bike boxes during a tour. Note: this fee can be avoided if you leave your box with your start/end hotel.

    Tandem Bike 
    a per bike fee for the extra logistics to handle a tandem bike that is brought by a guest.

    LIFECYCLE ADVENTURES LOCAL CYCLING GUIDES

    Reviews and Ratings

    Facebook Review image and link   Google Review image and link