Tuscany Bike Tour – Chianti Write a review
Join us on this cycling tour through Tuscany to explore its natural beauty, rich culture, and centuries of history. Relax in the grounds of an 18th century villa, enjoy a night out in Siena’s splendid Gothic centre, and stay in a former Renaissance monastery in charming Pienza. Tuscany’s romantic landscape makes for rewarding biking as each hill provides a view more beautiful than the last. Optional extensions allow 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. And of course, Tuscany is home to some of Italy’s best food and wine. (Start in Florence, 2 nights Panzano, 1 night Siena, 2 nights near Asciano, 2 nights Pienza)
Cycling is one of our passions, so it's no surprise that our Italian offices are located in one of the best biking areas in the world. We've spent decades in Tuscany so there isn’t a side road or café that we don’t know about. Join us as we show you our favorite rides through the hills and valleys of Chianti and the Val d'Orcia, past ancient hilltop towns, stone farmhouses, lone cypress trees and lush vineyards. At the end of the day celebrate with an excellent meal and a fine glass of wine. Combine the captivating landscapes of Tuscany with the exhilaration and freedom of biking.
Tuscany Bike Tour – Chianti itinerary
Meet your guides at 9:30 in Florence this morning for a bike fitting and the start of your first ride. We know the city well, so have a great way to get out of town and into the Chianti hills while avoiding the city traffic. Our destination is the village of Panzano in Chianti, where we stay at the hotel Relais Fattoria Valle, a beautiful 18th-century Tuscan manor house. Once home to a noble Florentine family, it has been restored and transformed into a lovely country hotel. The views from the garden and pool area are gorgeous, and it’s a great place to kick back and relax after a challenging day of riding the Tuscan hills. We dine in the hotel garden beneath a leafy canopy of plane trees. Overnight near Panzano. Hotel and dinner included.
Today we explore the hills and historic villages of Chianti, beginning with Radda, one of the cities in the Chianti League that helped Florence defend its territory from the Sienese during the Middle Ages. After a coffee break and some window-shopping, we continue on to Gaiole where we have lunch in the main square. Stop for a visit of a local ceramics producer on the way home, then return to your hotel. Late this afternoon we will visit the winery of Fattoria Le Fonti, a small, family-owned boutique winery owned and operated by my friends Guido and Vicki. After this special visit we will have dinner nearby. Overnight near Panzano. Hotel, breakfast and dinner included.
Today’s ride takes us through the tiny hamlet of La Piazza and then on to Castellina in Chianti for a mid-morning cappuccino. Your uphill efforts are rewarded by a fantastic downhill into the valley below. We stop for lunch at a local trattoria with a fabulous choice of pasta dishes and salads. We then ride to Siena and check into our hotel, La Colonna, which is situated just outside the medieval city walls and has a pool. We’ll have a visit of the city in the late afternoon, and then you are free to dine as you like tonight since it’s a “free night.” Overnight Siena. Hotel and breakfast included, dinner not included.
This morning we bike 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 first stop in the charming and authentic village of Asciano, an ancient walled town whose inhabitants have ingeniously incorporated the old defensive walls into their homes. After lunch we bike to our hotel, the Hotel Casabianca, a beautiful 4-star hotel in a renovated manor house featuring a lovely garden and gorgeous swimming pool. Relax by the pool and then meet up again for dinner. Overnight at the Hotel Casabianca. Hotel, breakfast and dinner included.
Today we have a loop ride to the beautiful Benedictine Abbey of Monte Oliverto Maggiore, whose monks are famous for their erudition and strict vows of silence. Visit the frescoed cloister and then enjoy a coffee in the garden before continuing on to lunch in the medieval village of Montisi. Optional extension ride or return to the hotel and enjoy some down-time by the pool or in the shady garden. Overnight at the Hotel Casabianca. Hotel, breakfast and dinner included.
Today we ride through the dramatic landscapes of southern Tuscany to the Renaissance gem of Pienza. The town was designed between 1459-62 following a decree by Pope Pius II in which Pienza was to become a showcase for Renaissance architecture and as such it boasts one of the earliest Renaissance cathedrals in Tuscany. It is also the heart of the local pecorino cheese production which goes so well with a glass of Vino Nobile from neighboring Montepulciano! On our way to Pienza we stop for lunch at the unique village of Bagno Vignoni, whose thermal springs have been treating Tuscany’s nobility for centuries. Our hotel will either be the four-star Relais Il Chiostro, an renovated cloister located inside the city walls with spectacular views over the countryside, or the recently restored Hotel Corsignano, just outside of the city walls. Dinner together in a local trattoria. Overnight Pienza. Hotel, breakfast and dinner included.
Our final day of cycling in Tuscany ends with a fantastic ride that takes us to the hilltop towns of the Orcia Valley. A sweeping downhill (and then uphill!) takes us to the lovely walled hamlet of Montichiello, where we can stop for a coffee break and enjoy breathtaking views over the valley. We then continue on to Montepulciano. Founded by the Etruscans 2,500 years ago, it continued to be a vital and important city well into the Renaissance. It sits high on a hilltop, so was the perfect location for the Medici to expand their power into southeastern Tuscany. We have lunch here, and you have time to explore the main squares, back alleys and shops before we meet up again to continue our ride back to Pienza. Tonight we get together for a final aperitivo and dinner together in town. Overnight Pienza. Hotel, breakfast and dinner included.
9:00 transfer to Chiusi for 10:00 trains to Rome, Florence and beyond. Breakfast and transfer included.
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.
The City of Florence: everything you need to know about the city.
The Accademia: home of Michelangelo’s David and other world-famous works and The Uffizi Gallery: one of the greatest collections in the world. We recommend you make reservations ahead of time. The official site for both the Uffizi and Accademia is http://www.polomuseale.firenze.it and http://www.Uffizi.org where in addition to ticket reservations useful information about the museum the artworks, the events,
and what visitors need to know before visiting the gallery.
The Duomo: one of the wonders of the Renaissance, Florence’s cathedral.
Siena: 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
Monteriggioni: more information on this fascinating hilltop fortress
UNESCO World Heritage Sites: Italy has more sites listed than any other country!
Activity Rating: This trip is rated 4 out of 5. 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.
Trip Cost Includes: 7 nights' accommodations (2 nights Panzano, 1 night Siena, 2 nights Asciano, and 2 nights Pienza in comfortable 3 & 4-star hotels with swimming pool); 7 breakfasts and 6 dinners; bilingual guides; support vehicle; all visits as noted in the itinerary; all luggage transfers and final transfer to Chiusi train station at the end of the trip; and hybrid bicycle rental (road bikes are available for a small supplement). All departures are accompanied by two guides.
Booking: e-mail us at email@example.com to receive a booking contract (or use the 'Contact Us' link at the top of this page), or click on the 'Book Now' button to the right.
Insurance: We highly recommend the purchase of Trip Insurance. We recommend “Travel Guard” to our North American clients, just click on the logo below. Australian, New Zealander, and British travelers, please consult your insurance brokers.
Getting There: the trip starts in Florence at 9 a.m. Florence is well connected by road, rail and air with the rest of Italy and Europe.
Air: Florence airport receives both domestic and international flights through European hubs such as London, Paris, Frankfurt, Amsterdam, Munich and Brussels. You can also fly into Pisa (about an hour away by train) on many low-cost airlines. For a complete list of Italian airports and a selection of low-cost airlines, see our "Transport Info" page.
Rail: The Eurostar and new Italo high-speed trains connect Florence with Milan (travel time about 2.5 hours), Bologna (travel time 35 mins) and Rome (travel time 1.5 hrs). See the Trenitalia website (in English) at this link. For alternative high-speed rail travel, see the Italo website. For complete information on using the Italian train system, see our blog post.
Road: The A1 Autostrada connects Florence with the rest of Italy. Travel time from Milan is about 5 hours, from Bologna 1.5 hours, and from Rome about 3 hours.
Getting Away at the End of the Trip: the trip ends with a van transfer to the Chiusi train station after breakfast on Saturday. We arrive around 10:00 a.m. to make connections to Florence, Rome, or other destinations.
If you book a trip with us you will receive detailed information about how to get to and from the trip, and of course you can e-mail us with any questions.
I was thoroughly satisfied with this tour! The itinerary was very well planned and thought through, the food and wine were fantastic, and our guide took terrific care of us. The biking was challenging, but the amazing scenery made it all worthwhile. Tuscany is a wonderful place to visit, and Customwalks' tour was a great way to experience it.