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Tuscany Self-Guided Bike Tour

Val d'Orcia to Chianti, the trip of your dreams

Tuscany is more beautiful than you can imagine. As you ride along winding cypress-lined roads, golden rolling hills reveal their gentle majesty before you. Ancient farms, vineyards, and valleys bask quietly in natural sun-kissed splendor. Tranquil hilltop villages await discovery behind medieval walls. With a cuisine as simple as it is delicious, a proud tradition producing some of the world’s finest wines, and a people blessed with profoundly friendly hospitality, Tuscany has a magic that instantly enchants you to relax and savor every exquisite, precious moment. If you are seeking adventure but don't want to worry about how to make it happen, Trek Travel's self-guided bike tour in Tuscany offers an incredible itinerary to discover the wonders of this truly magnificent land at your own pace. Book your trip with confidence »

Learn more about Self-Guided trips and if they're right for you» or discover a perfect day in Tuscany»
$2899 Per Person
6 Days & 5 Nights
Rider Type: ?
3 - Active Non-riders Welcome
From $2899 per person View All Details
Trip Wows
Ride along quiet roads lined with cypress trees in the beautiful Tuscan landscape
Stay in 15th-century palaces which have been transformed into charming and elegant hotels
Walk through the red-brick streets of medieval Siena and learn about the Palio di Siena, the famous horse race
Pamper yourself with the best Chianti wines in the heart of the Chianti region
Indulge in the fresh pasta dishes of the Tuscan cuisine and discover local pecorino cheese
A very well-conceived trip with fun routes, excellent food, and interesting side tours. We felt Trek was fully behind us whilst enjoying the freedom of self-guidance. And the Trek bikes inspired confidence!
-John, Trek Travel Guest

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price and date are guaranteed.
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Single Occupancy
Available for 2021. Our trip on your schedule. Simply choose your own travel dates and we will handle the rest. Price based upon double occupancy and may vary based on hotel availability and dates requested. Contact us at 866-464-8735 to get started.
Don't see your ideal travel date? 
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:
2020 - June 1, 2021 Departures:
  • 6+ Guests    Price as advertised*
  • 4-5 Guests +$500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
  • 1 Guest        Call us for pricing*

2021 Departures After June 1, 2021:
  • 10+ Guests Price as advertised*
  • 8-9 Guests +$500 per person to trip price*
  • 6-7 Guests +$1,000 per person to trip price*
  • 4-5 Guests +$1,500 per person to trip price*
  • 2-3 Guests +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Looking for a date that you don’t see?
Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

Meet your Trek Travel guide at the boutique hotel Palazzo del Capitano, located in the heart of the medieval village of San Quirico d’Orcia. Together with your guide you will walk to a local trattoria for lunch, where you'll get a brief orientation of the week ahead. Following lunch you may change into your cycling gear and your guide will fit you to your Trek bike, ensuring your comfort on your bike for the week. Then, it's off on your first self-guided adventure in the enchanting landscape offered by the Val d’Orcia, famous for the unique and pristine views where cypress-lined country roads have become the worldwide representative image of the Tuscan countryside. Your first stop is the tiny medieval spa town of Bagno Vignoni, where you can dip your toes in the famous thermal springs and take pictures of the Roman baths located right at its center. Continue this scenic loop with a gentle climb up to Pienza, a UNESCO Site renowned for its Pecorino cheese and considered one of the symbols of the Italian Renaissance. Wander through its streets and grab the best gelato at “Buon Gusto” before cycling back to your hotel at your leisure. Take some time to relax by the pool with a glass of wine and afterward we suggest you walk to our favorite restaurant in the heart of San Quirico to enjoy your first Tuscan dinner!

Today's Ride:

San Quirico to Bagno Vignoni to Pienza Loop
Approximately 18 miles with 1,400 feet of climbing


Palazzo del Capitano

Included Meals:


This morning’s route lifts you high above the Val d’Orcia, a vista dotted with rolling hills blanketed with vines and rows of cypress trees. After passing by the spa town of Bagno Vignoni, you will ride up to Castiglione d’Orcia, admiring the remains of what was once the mighty Rocca Aldobrandesca, a fortress that dominates the village. Your first stop today will be the renowned Abbazia di Sant’Antimo, a monumental 12th-century Romanesque abbey, where if you're lucky, you may arrive to the haunting choral harmonies of the monks' Gregorian chants—magical! Your lunch destination is the walled village of Montalcino with its 14th-century fortress and steep cobblestone streets that dominate the surrounding countryside. Here you can discover the delights of Brunello wine, one of the finest Italian varietals and enjoy lunch at your leisure at one of Montalcino’s many trattorias. When you're ready, cycle back to San Quirico along winding roads and relax at the hotel before selecting a local bistro in town from the list of Trek Travel recommendations.

Today's Ride:

San Quirico to Montalcino Loop
Approximately 34 miles with 3,900 feet of climbing

Avid Option:

San Quirico to Montalcino Loop w/ Monticchiello
Approximately 54 miles with 5,400 feet of climbing


Palazzo del Capitano

Included Meals:


Today you’ll head north into one of Italy’s most dramatic regions, the Crete Senesi, following winding ribbons of road into gently undulating terrain. Once you leave San Quirico, your luggage will be transferred to your next hotel and you will find it already in your room upon arrival. Enjoy the luxury of travelling worry-free and focus on your ride, where vineyards and olive trees give way to cultivated fields crossed occasionally by rows of cypress trees and a few solitary farmhouses. The particular dry grey terrain forms a sort of badlands typical of this area, which appears almost lunar, and are distinguished by the dramatic colors of the clay-dense soil. At the same time a barren landscape yet also some of the most stunning views in Tuscany. Riding here gives you a feeling of peace and, if you feel like adding some more elevation, take the avid route to Monte Oliveto Maggiore, a 12th-century splendid Benedictine abbey situated in a beautiful position overlooking the surrounding ridges. After a visit to the abbey, continue steadily downhill to Asciano where you can refuel with a delicious meal at one of its numerous trattorias before heading to Siena, a medieval jewel made of red-brick lanes tumbling every which way. Take a moment to relax at the hotel before taking a stroll through Siena. Make sure you walk to Siena’s most impressive attraction, Piazza del Campo, a shell-shaped square dominated by a stunning Gothic Duomo that is a real feast for the eyes. From this location, an array of Tuscan specialties are at your fingertips. Just choose the restaurant that best suits your tastes tonight!

Today's Ride:

San Quirico to Siena
Approximately 41 miles with 3,900 feet of climbing

Avid Option:

San Quirico to Siena with Abbazia Monte Oliveto
Approximately 47 miles with 4,700 feet of climbing


Hotel Athena

Included Meals:


Enjoy your morning cappuccino and say goodbye to Siena! While we take care of transferring your luggage to your next hotel, you can enjoy today’s ride traversing the forested hills and olive groves of the Chianti region. Pedal through the village of Lecchi and enjoy an espresso with the locals before continuing up to Radda, the ancient capital of the League of Chianti. Spend some time in Radda to explore this vibrant village, filled with bustling shops and galleries—the perfect place to pick up some mementos to bring home. If you want to buy a local bike jersey Gianni’s shop offers the best selection of cycling kits, so don’t miss this opportunity! We recommend a lunch stop at our favorite place, Bar Dante, where the hosts Fabrizio and Carolyn pride themselves on serving the best bruschetta in Radda, washed down with a glass of local Chianti. Following lunch continue your ride at your own pace to Castellina in Chianti, one of the most charming towns in the Chianti region, known for its cultural heritage and for the production of wine and olive oil. Tonight, choose from the list of our recommended restaurants in Castellina, all walking distance from the hotel. Whatever option you choose, it is going to be an exquisite dinner in the magical atmosphere of the Chianti region.

Today's Ride:

Siena to Castellina in Chianti
Approximately 31 miles with 2,900 feet of climbing

Avid Option:

Siena to Castellina in Chianti via San Gusmé
Approximately 41 miles with 4,800 feet of climbing


Palazzo Squarcialupi

Included Meals:


For over 200 years, the Chianti area was a prime battleground for fights between Siena and Florence. Castles and walled towns were built on hilltops as protection and to maintain control over the land. Today, after a beautiful morning descent, you will pedal on quiet country lanes past Passo dei Pecorai (Pass of the Shepherds) to reach Castello di Verrazzano, a castle that welcomes visitors and wine connoisseurs with its cellars dating back to the 16th century. Your lunch destination today is the lively town of Greve in Chianti with its triangular-shaped square and stone pavement. Take in the small-town atmosphere as you enjoy a well-earned lunch at the restaurant of your choice, living an authentic Chianti experience! After lunch, you can take the avid option to the castle of Lamole and rejoin the regular ride in Panzano before heading back to the hotel. Enjoy an afternoon of relaxation with a drink on the hotel terrace overlooking the sun-drenched hills. This evening is yours to wander the cobblestone streets of Castellina before discovering the “Via della Volte”, an impressive, historic, underground tunnel which is now a fascinating walkway filled with artisan boutiques and restaurants. Here you may enjoy a wine-tasting of Chianti wines savoring the unique flavours of this magical land before one last dinner in town.

Today's Ride:

Castellina in Chianti to Greve Loop
Approximately 36 miles with 3,700 feet of climbing

Avid Option:

Castellina in Chianti to Greve Loop w/ Lamole Castle
Approximately 43 miles with 4,600 feet of climbing


Palazzo Squarcialupi

Included Meals:


If you're up for it, close out your Tuscany self-guided bike tour by rising early for a final bike ride to Poggibonsi as you watch the sunrise creeping over the classic Tuscan countryside. Or simply linger over a hot cappuccino and walk into town at your leisure enjoying this enchanting region. A Trek Travel guide will meet you at the hotel at 11:00 AM to take your bike and say farewell before you leave for Florence or other destinations.

Today's Ride:

Castellina in Chianti to Poggibonsi Loop
Approximately 22 miles with 2,300 feet of climbing

Included Meals:



hotel image

Palazzo del Capitano

San Quirico d’Orcia, Italy

Set just inside San Quirico d'Orcia's historic town walls, Palazzo del Capitano is a charming 15th-century building transformed into an elegant 4-star hotel, joining tradition with modern comforts. The property is surrounded by olive groves and Mediterranean gardens where you will find plenty of opportunity to lounge in the sun. This historic palazzo boasts newly renovated rooms, an indulgent spa, tranquil gardens, and an ideal location. Its mix of modern luxury and rich history is sure to enchant you.
hotel image

Hotel Athena

Siena, Italy

This 4-star hotel is nestled among the heart of the old town, with the Cathedral and Piazza del Campo only steps away. It has been designed with luxury and rustic sensibility in mind, as each room comes equipped with a range of modern amenities. Enjoy panoramic views of the Tuscan countryside from a rooftop terrace adjacent to the hotel bar.
hotel image

Palazzo Squarcialupi

Castellina in Chianti, Italy

Located in the medieval heart of Castellina in Chianti, one of central Tuscany’s most charming villages, the hotel boasts a remarkable view of the stunning Chianti hillsides, a beautiful garden with an outdoor swimming pool, and a spa. The rooms of Palazzo Squarcialupi, a 15th-century palace, feature rustic terracotta floors, exposed wooden beams on the ceilings, and 18th-century furnishings highlighting the hotel’s original structure.

What's Included

For us, the details matter most

Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.


Trek Domane SL 7 Disc

It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. In 2019, we upgraded our fleet to feature the award-winning Domane SL 7 with Shimano Ultegra Disc brakes. Because when you combine the lightweight stability and comfort of the Domane with the superior safety and stopping power of disc brakes, you get a match made in cycling heaven. And the best part? It’s included in the trip price. Ride confidently, comfortably and longer in the most beautiful destinations around the world with the new Domane SL 7. Learn More


Trek Electric-Assist Domane+ LT

The Domane+ LT combines the best of the race-built Domane endurance bike with a slight pedal-assist perfect for climbing the toughest hills. This bike primarily functions as a road bike, but on tough hills or in strong headwinds, you can get an extra boost by using the electric assist feature. Learn More


Trek Electric-Assist Verve+

With its Low-Step frame design, hopping on and off the Trek Verve+ is super easy. The front suspension will take the edge off any bumps in the road and the Bosch system will keep you smiling from ear to ear. The integrated battery keeps this bike looking sleek as you pedal through amazing terrain. Learn More


  • Five nights of accommodation at handpicked hotels
  • Daily breakfast
  • Day 1 lunch with the guide
  • Daily lunch and dinner recommendations
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily route options on riding days
  • Trek Travel water bottles to keep
  • Trek Travel Bontrager cycling jersey to keep
  • Each bike is equipped with a flat pack, frame pump, phone mount, front and rear lights
  • Bontrager helmet (optional if you do not bring your own)
  • Bontrager saddle (we suggest you bring your own for the most comfortable fit)
  • Shimano clipless pedals or flat pedals (optional if you do not bring your own)
  • All luggage transfers during your trip
  • A bike lock, all necessary chargers and a floor pump
  • Bike fit on the first day to help you find your optimal position for comfort, with recreational or avid set-up along with saddle preference
  • Ride With GPS app on your phone to navigate and get all the information you need on your self-guided adventure
  • Optional daily phone or video call with the guide to prep you for the next day’s adventure
  • Support on the ground in case of emergency


  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+, available in a limited quantity
  • Trek Travel Bontrager cycling jersey to keep
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, or flat pedals (optional if you do not bring your own)
  • Bontrager helmet (optional if you do not bring your own)
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights
  • Each bike is equipped with a flat pack, frame pump and phone mount
  • A bike lock, all necessary chargers, and a floor pump
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip.
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your guides will install your gear on the first day during your bike fit.


Gratuities for your Trek Travel guide are not included in your trip price. We recommend tipping 7.5-10% of your trip price, preferably in the local currency. Please tip your guide at your discretion, based on their level of professionalism, guest care, and service.
  • Airfare and transportation to and from the trip meeting/departing locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • While we provide daily breakfast and one lunch, the other meals are not included. On self-guided trips, Trek Travel provides restaurant recommendations and invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

30 miles
182 miles
3,000 feet
18,265 feet
The terrain is consistently rolling, with quiet, narrow, and winding roads. Many towns sit atop hills and, although the ascents are not exceptionally steep, they are often upwards of five kilometers long. Our Tuscany self-guided bike tour is best suited for our Type 3 Riders. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option—you still get a workout but can climb alongside even the strongest rider. Type 4+ Riders will enjoy the extra mileage the avid route options offer.
There are a variety of non-riding options on this trip for riders who want to take the afternoon off or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Except as specified in the itinerary, expenses and transportation to these activities are not included in the trip price. Some non-riding options on this trip are:
  • Shop and explore the medieval villages of Pienza, San Quirico, Radda, Lecchi, Montalcino
  • Relax by the pool
  • Enjoy a stroll through medieval Siena
  • Explore the walled city of Castellina
  • Enjoy a wine tasting of the renowned Tuscan wines in the heart of Chianti

See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel seeks to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times, routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our Today’s Ride options.

Travel Details

How to Get There

Amerigo Vespucci (Florence) Airport (FLR)
11:00 AM
Hotel Palazzo del Capitano, San Quirico d'Orcia

Say Farewell

Amerigo Vespucci (Florence) Airport (FLR)
11:00 AM
Hotel Palazzo Squarcialupi, Castellina in Chianti


We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into Florence’s Amerigo Vespucci Airport (FLR). The Florence airport is about three miles from the town center. You can take a taxi (approximately 20 euros) to the centre of town, or a bus which departs hourly.

Rome and Milan also offer flight options. From Rome’s Fiumicino Airport (FCO), you may take a direct train to Rome’s central station, Roma Termini. Follow the “Stazione/Railway Station” signs. Trains depart twice hourly. Tickets can be purchased at a Biglietteria office or from ticket machines. All tickets must be validated before getting on the train: do this by stamping your ticket at the yellow boxes near the platform. The ride takes 30 minutes. Taxi service is available from Rome Fiumicino Airport to central Rome for approximately 50 euros. From Roma Termini, transfer to a train for Florence. The Frecciarossa trains depart frequently and are the quickest. The trip takes an hour and a half and costs between 44-62 euros one way per person.

The trip takes place in the Tuscan countryside that is not well served by public transportation. The best way to get from Florence to your trip hotel in San Quirico d'Orcia is by private shuttle. We suggest you contact our local driver ahead of time to arrange the transfer and mention you are traveling with Trek Travel. Our Trip Consultant can provide you with our recommended local contact information. The trip takes about two hours and costs €200. You can pay with credit card but American Express is not accepted.

Alternatively you may take a train from Florence to Siena (which takes about 90 minutes and costs about €10), followed by a taxi ride to San Quirico d'Orcia. The private transfer from Siena to San Quirico takes about 1 hour and costs approximately €100. We suggest you contact our local driver ahead of time to arrange the transfer. Our Trip Consultant can provide you with our recommended local contact information.

Your Trek Travel guide will meet you at the hotel Palazzo del Capitano (Via Poliziano, 18, 53027 San Quirico d'Orcia SI) at 11:00 AM on the first day of the trip. Together you will walk to a local trattoria for lunch and your guide will give you a brief orientation of the week ahead. After lunch you may change into your cycling gear and your guide will fit you to your Trek bike ensuring you find your optimal position for comfort for the week. After a safety talk, saddle up to begin the day's ride through the Tuscan countryside.

If you will be late for the pick-up or are going to miss it altogether, please inform your guide. You will receive an email a week before the trip start with their name and contact details. If you cannot reach them, please call our first hotel, Palazzo del Capitano (+39 0577 899028) and leave a message with your expected arrival time and contact details.

View our pre hotel recommendations


A Trek Travel guide will meet you at 11:00 AM at the hotel Palazzo Squarcialupi (Via Ferruccio, 22, 53011 Castellina in Chianti, SI) to take your bike and equipment before your departure. The hotel staff will be happy to reserve a taxi for you for Florence. The trip takes approximately one hour and costs about € 110. Please, do not schedule a flight prior to 3:00 PM.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

Spring and fall in Tuscany are usually clear and sunny, with warm daytime temperatures (75F-90F) and evening temperatures 10-15 degrees cooler. A jacket or wrap will be useful in the evening. Summers are hotter with higher daytime temperatures (80F-95F) and evening temperatures 10 degrees cooler. Rain is always a possibility, so be prepared with wet-weather gear in order to best enjoy your vacation. Packing List

Before and After Your Trip


Before: Florence, Italy

Florence is the majestic heart of Renaissance art and intellect. Several days can be spent wandering the streets in the shadow of Brunelleschi’s Duomo and strolling beside the Arno. Along with the Duomo and Ponte Vecchio, the Uffizi gallery, a pillar of the Renaissance and Medici eras, merits a visit. Michelangelo's David in the Galleria dell'Accademia is not to be missed. Keep in mind while exploring Florence that opening hours vary and are quite often inconsistent. Different museums are open on different days and lines can be very long. It’s worthwhile to pay a few extra euros and pre-book your tickets—this will enable you to bypass long lines of visitors at the entrances. We recommend the following accommodations for your pre-trip hotel:


After: Rome, Italy

Rome is a powerhouse of stunning architecture and ancient history, beautifully told through its ruins and buildings. It seems that every street you walk down provides another unexpected glimpse of ancient times, yet modern bustle and energy abounds as well. The Coliseum, the Forum, Vatican City, and the Pantheon are some of the must-see attractions. Be sure to linger on the Spanish Steps one afternoon and take advantage of great shopping and fantastic cuisine. We recommend the following accommodations for your post-trip hotel:

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the ultra-smooth Trek Domane SL 7 to the Trek Electric-Assist Verve+, you deserve the best ride on your vacation. Plus, we offer a range upgrade options to take you the extra mile.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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