- 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 +$2,500 per person to trip price*
After a one-hour shuttle from Florence, you will arrive at the boutique hotel Palazzo del Capitano located in the heart of the medieval village of San Quirico d’Orcia, where you will be welcomed by a Trek Travel guide. We will ensure that you have an excellent fit to your Trek bicycle and offer specific cycling tips for riding in Italy. Then, it's off on your first self-guided adventure in the enchanting landscape offered by the Val d’Orcia, famous for its beauty and 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 famous for its Pecorino cheese and considered one of the symbols of the Italian Renaissance with the geometry of its design in perfect harmony with the magnificence of the surrounding landscape. 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 walk to our favorite restaurant in the heart of San Quirico to enjoy your first Tuscan dinner!
San Quirico to Bagno Vignoni to Pienza Loop
Approximately 18 miles with 1,400 feet of climbing
Palazzo del Capitano
Social Hour | Dinner
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 dominating 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 Trek Travel recommendations.
San Quirico to Montalcino Loop
Approximately 34 miles with 3,900 feet of climbing
San Quirico to Montalcino Loop w/ Monticchiello
Approximately 54 miles with 5,400 feet of climbing
Palazzo del Capitano
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. The vineyards and olive trees will give way to cultivated fields crossed occasionally by rows of cypress trees and every so often you will see a solitary farmhouse. The particular dry grey terrain forms badlands, typical of this area, which recall a "moonscape", distinguished by the dramatic colors of the soil and blessed with 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 venturing on a walking tour of Siena with a local guide and discover the secrets of this historic city. The tour will finish at 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 practically at your fingertips. Just choose the restaurant that best suits your tastes tonight!
San Quirico to Siena
Approximately 41 miles with 3,900 feet of climbing
San Quirico to Siena w/ Abbazia Monte Oliveto
Approximately 47 miles with 4,700 feet of climbing
Guided walking tour of Siena
Enjoy your morning cappuccino and say goodbye to Siena! Today’s ride traverses 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 oil. Tonight, you'll savor an exquisite meal at the hotel's restaurant, soaking in the magical atmosphere of the Chianti region.
Siena to Castellina in Chianti
Approximately 31 miles with 2,931 feet of climbing
Siena to Castellina in Chianti via San Gusmé
Approximately 41 miles with 4,800 feet of climbing
Breakfast | Dinner
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 with its triangular-shaped square and stone pavement. Take in the small-town atmosphere as you enjoy 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 and 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. Savor the picturesque views and unique atmosphere of this charming village with one last dinner in town!
Castellina in Chianti to Greve Loop
Approximately 36 miles with 3,700 feet of climbing
Castellina in Chianti to Greve Loop w/ Lamole Castle
Approximately 43 miles with 4,600 feet of climbing
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 enjoy a leisurely morning enjoying this enchanting region. A Trek Travel guide will meet you at the hotel at 10:00 AM to take your bike and say farewell before you board on a private shuttle to Florence.
Castellina in Chianti to Poggibonsi Loop
Approximately 22 miles with 2,300 feet of climbing
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.
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
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
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
See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel strives 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.
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 (~20 euros) directly to the hotel, 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. From Roma Termini, transfer to a train for Florence. The Eurostar trains depart frequently and are the quickest. The trip takes 1.5 hours and costs between 44-62 euros one way per person. In Florence, taxis are available to take you to your hotel. Taxi service is available from Rome Fiumicino Airport to central Rome for ~50 euros.
A private shuttle will pick you up at the Hotel Montebello Splendid (Via Giuseppe Garibaldi, 14, 50123 Florence, Italy) at 11:00 AM on the first day of the trip. Should you wish to reserve a room at this hotel pre-or post-trip, please contact your Trip Consultant for a discount code. You’ll then shuttle 90 minutes to your first trip hotel in the Val d'Orcia, where a Trek Travel guide will meet you. You will receive a personalized bike fitting to ensure your comfort on your Trek Domane for the week, before you take your first spin through the Tuscan countryside.
If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip start with their names 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. You may take a taxi to the first night’s hotel for approximately 200 euros. The trip takes almost two hours from the center of Florence.View our pre hotel recommendations
A Trek Travel guide will meet you at 11:00 AM at the hotel Palazzo Squarcialupi to take your bike and equipment. You’ll depart by private shuttle for Santa Maria Novella train station where trains connect to many European cities. Please do not book seats before 1:30 PM, allowing adequate connection time for any ongoing travel or possible traffic delays. The airport in Florence (FLR) is three miles from the city. You can reach it by train, taxi, or shuttle bus; please do not schedule a flight prior to 4:00 PM. Visit www.TrenItalia. for train information.View our post hotel recommendations
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
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.
In every region we travel, we uncover the area’s best and most delightful accommodations. On our Tuscany trip, you will stay in a historic palazzo in charming San Quirico, a luxurious country villa surrounded by rolling hills, and a former castle of a medieval hamlet high above Gaiole. We recommend the following accommodations for your post-trip hotel.
Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, to our numerous upgrade options, you deserve the best ride on your vacation.
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.
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.