Tuscany Bike Classic

We designed this trip to highlight the wonderful fusion of Tuscany's natural beauty with its rich culture and centuries of history. During the trip you will stay in a variety of accommodations: an 18th century country villa, a modern hotel in the beautiful Gothic city of Siena, a small medieval walled village, and finally in Montepulciano, a majestic hilltop town famous for its excellent wines. The trip is also suited for people who really like to ride. Tuscany is hilly and therefore the riding is challenging but also extremely rewarding, as each hill provides a view more beautiful than the last. We have developed optional extensions for each day of riding that enables keen riders to get as much mileage as they want, while less experienced riders have the reassurance of our support van which is available to assist when needed. Of course, the van also moves your luggage.

(Luggage transferred by van. 2 nights Villa Lecchi, 1 night Siena, 2 nights Asciano and Montepucliano. Trip ends at Chiusi train station.)


Day 1 - Saturday: Make your way independently to the Hotel Villa Lecchi. The Villa is located just a few kilometers from the town of Poggibonsi, which is easily reached by bus or train from both Florence and Siena. From Poggibonsi, take a taxi to Villa Lecchi and relax in their garden or by the pool overlooking the countryside. Meet your guides and the rest of the group at 7:00 p.m. for an aperitivo. The guides will give a short introductory talk and then we will have dinner in the dining room. Hotel and dinner included.


Day 2 - Sunday:  Meet your guides after breakfast at 9:00 a.m. for a bike fitting and safety talk, then start off on your ride to the medieval village of Castellina in Chianti, a fortified hill town famous from Etruscan times. There is a long gradual uphill which rewards you with stunning views over the Tuscan landscape. Ride through the vineyards and olive groves of the famous Chianti region, then relax by the pool at the Villa Lecchi before dinner. Overnight Villa Lecchi. Hotel, breakfast and dinner included.


Day 3 - Monday: Today's ride takes us out of Chianti and into the hills east of Siena. We stop for a coffee break at the 12th century fortress of Monteriggioni, so impressive it earned a mention in Dante's "Inferno". We continue up into the hills, stopping for a picnic in a lovely chestnut grove, before heading to the Hotel La Colonna just outside the city walls of Siena. In the afternoon, take a stroll through town, have a swim, or just relax at your hotel. Tonight is a "free night," so you can take your pick of Siena's fabulous cafés, restaurants, and trattorias. Overnight Siena. Hotel and breakfast included.


Day 4 - Tuesday: This morning we offer a guided visit of Siena, so you can learn about the history and culture of this amazing city as well as the importance of its Palio horse race. After lunch in Siena we change into our bike clothes and start our ride to Asciano. We head into a terrain that is completely different from what we have seen so far, and enter the clay hills of the Crete Senesi. Those who have seen the films Stealing Beauty or The English Patient will recognize this starkly beautiful landscape of barren rolling hills punctuated by solitary cypress trees. We stay in the charming and authentic town of Asciano, which has everything we love about Tuscany: cute cobblestone streets, medieval walls, Etruscan ruins, Roman mosaics, a hotel with a pool, and even a bike shop! We have a wine tasting tonight, then dinner at a local restaurant. Overnight Asciano. Hotel, breakfast and dinner included.


Day 5 - Wednesday: Today we ride to the beautiful Abbey of Monte Oliveto Maggiore, founded in 1313 by Giovanni Tolomei of Siena. Upon arrival at Monte Oliveto we will visit the Great Cloister (1426-74), featuring a fresco cycle relating the life St. Benedict. We then continue through the wheat fields and chestnut forests to the medieval village of Montisi for lunch. Our afternoon ride takes us through Trequanda before dropping us back down into Asciano. Dinner tonight features an Italian favorite - pizza! Overnight in Asciano. Hotel, breakfast and dinner included.


Day 6 - Thursday: Another day of riding helps us transfer to the striking hilltop town of Montepulciano. We cycle down small roads that wind their way up, over, around, and between tiny villages set amidst the olive groves and vineyards. Our hotel is located inside the walls of Montepulciano and affords expansive views to the south over the Orcia Valley towards Lago Trasimeno. Take some time this afternoon to explore the town's labyrinth of narrow medieval streets and enjoy an aperitivo in the main piazza before a "free night" dinner on your own or with new friends. Overnight Montepulciano. Dinner not included. Hotel and breakfast included.


Day 7 - Friday: Our final day of riding is fantastic. We cycle down into the Orcia Valley and stop in Pienza for a short visit. Pienza was designed between 1459 and 1462 by Pope Pius II, a local boy who rebuilt his hometown and named it after himself! He decreed that Pienza be a center of art and humanist values, and its Duomo was one of the first Renaissance cathedrals in Tuscany. We then ride back down into the valley then up to the adorable village of Monticchiello for a cold drink and spectacular views over the valley. We bike back to Montepulciano then get together for drinks and dinner, accompanied of course by the town's famous Vino Nobile di Montepulciano. Overnight Montepulciano. Hotel, breakfast and dinner included.


Day 8 - Saturday: Transfer by van to Chiusi train station for 10:00 trains to Rome, Florence, and beyond. Breakfast included.


See all of our tours by DESTINATION & ACTIVITY
See all of our tours by date: TOUR CALENDAR 2009

The biking in Tuscany is hilly! We sometimes ride sustained climbs of 10-15 kms, with some steep grades.  We ride 40 - 65 km a day, with optional extensions as well as van support, which allows you to relax off the bike for a while. We have designed the trip so that there is always some free time in the late afternoon so you can relax, read, or explore the towns where we stay. Breakfast is included every day, and dinners reflect the excellent traditional food of the region.


Useful Links -
The City of Florence:  everything you need to know about the city
The Accademia: home of Michelangelo's David and other world-famous works
The Uffizi Gallery: one of the greatest collections in the world. We recommend you make reservations ahead of time.
The Duomo: one of the wonders of the Renaissance, Florence's cathedral.
Siena Tourist Authority: this site has interesting links to areas within Siena province, like Chianti, the Val d'Orcia, & the Crete Senesi
Chianti Classico wine corsortium:  a site devoted to this world-renown wine and its group of producers
Chianti History:  concise article on the history of this famous region
Monteriggioni:  more information on this fascinating hilltop fortress
UNESCO World Heritage Sites: Italy has more sites listed than any other country!

General Information

Qualifications: This trip is rated Challenging. Tuscany is very hilly, so you must enjoy biking -- including up hills! The daily distances are between 45-65 kms (28-40 miles), or about 3-5 hours of riding divided between morning and afternoon. Trip Cost Includes: All accommodations in three star hotels (2 nights Villa Lecchi, 1 night Siena, 2 nights Asciano, 2 nights Montepulciano); 7 breakfasts and 5 dinners (2 "free night" dinners, in Siena and Montepulciano), bilingual guide or guides; support vehicle; guided tours as noted in the itinerary; all luggage transfers, final transfer to Chiusi train station at the end of the trip; bikes (quality 27-speed hybrid-style touring bikes with front handlebar bags and rear racks). Getting there (this will redirect you to our "Getting to the Trip" page) Booking: e-mail us to receive a booking contract (or use the "Reservation" page).  Insurance: We highly recommend the purchase of Trip Insurance. We recommend "Travel Guard" to our American clients, just click on the logo below, while Canadian residents can click here.  Australian, New Zealander, and British travelers, please consult your insurance brokers. We look forward to having you join us for the trip of a lifetime!