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.

We love Tuscany so much that our Italian office is located right here in Chianti, so there isn't a side road or café that we don't know about. Biking is one of our passions, so it is no accident that we are located here in some of the best biking country in the world. Why not join us and let us show you around?


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 cobblestoned 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.


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 consortium: 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

Note on Itinerary: Although we do our best to adhere to the schedule listed above, this itinerary is subject to change for numerous reasons beyond our control. Qualifications: This trip is rated Challenging. Tuscany is very hilly, so you must enjoy biking -- including up hills! If you ride 2-3 times a week and are relatively fit you will enjoy this trip. The daily distances are between 45-65 kms (28-40 miles), which translates into 3-5 hours of riding more or less equally divided between morning and afternoon. This may sound like a lot, but we make frequent stops to take pictures, enjoy a cappuccino, or simply enjoy the view. You are provided with written route directions, which allow you to be independent and ride at your own pace. However, a regular conditioning program consisting of cycling, walking/running and a daily stretching regimen is recommended, beginning at least 3 months prior to departure. This will get you in shape and ensure that you are comfortable in the saddle, allowing you to enjoy all that this wonderful trip has to offer. In other words, get your bum used to a bike seat before you arrive to avoid suffering during the trip! There is a support van to move the luggage and also to help tired bikers in case of need. Most importantly, the rides are absolutely beautiful! We have gone to great lengths to find the most scenic yet least trafficked routes for our rides. We love the region so much, our Italian office is based in Chianti! The Bikes: Our hybrid bikes are lightweight Carraro "Azumut 706" aluminium frames with high-end Shimano Deore and Deore LX componentry (with an aluminium fork, not a suspended fork). They are very comfortable, with a relatively upright riding position as well as climbing bars which enable you to change your hand position. They have 27 speeds with index shifters on the handlebars. They have a low gearing ratio to make hill climbing especially easy, and the upright sitting position reduces shoulder and neck fatigue. A more upright position also means that you get to look at the beautiful countryside instead of just the asphalt in front of your wheel! The bikes come with a small front handlebar bag suitable only for light things, a separate map case, water bottle, pump, spare tube, and a rear carrier rack. We HIGHLY recommend that you bring a strap-on rear carrier bag that sits on top of the rear rack (not a side panier). You can bring your own pedals and seat, which we can mount for you. The bikes are sized based on the information that you send to us, so be as accurate as you can! You must bring your own helmet. Please check the Carraro website if you are interested in our hybrid bikes. Road bikes (with a triple chain ring) are also available for a small extra charge. If you would like more detailed info from our bike geek, please send him an e-mail. Weather: We have scheduled our departures to avoid mid-summer heat and crowds while still enjoying ample sunshine. Temperatures during our visits generally range from 75° to 85° F during the day, dropping approx. 10 degrees at night. Some rainfall is possible on any of the departures requiring participants to arrive equipped with appropriate raingear (see Gear List). 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). Not Included: Round-trip airfare; airport/hotel transfers; lunches; travel insurance; gratuities; alcoholic beverages and items of a personal nature. Please bring your own bike helmet, as you will be required to wear one. Getting there (this will redirect you to our "Getting to the Trip" page) General Information: This trip is subject to the booking information set forth in the CustomWalks Ltd. reservation information and trip agreement. Please read this information carefully and e-mail us (or use the "Contact Us" page) if you have any questions. We highly recommend the purchase of Trip Insurance which you can do through CustomWalks Ltd or by clicking on the logo below (another window will open up on your screen). We look forward to having you join us for the trip of a lifetime! Why wait? Space is limited. Send us an email or fax to reserve your trip. Full trip details including detailed pre-departure information, train timetables, and a gear list are sent upon receipt of deposit. Come join us!