Tuscany Bike Tours
The Flowered Heart of Italy
Tuscany, a celebrated region in central Italy, has been at the heart of European culture since the Middle Ages and the rise of the Grand Duchy.
The area is not only famed for its rolling hills and fertile vineyards, but also for its medieval towns, Renaissance heritage, and architectural landmarks, from the iconic Leaning Tower of Pisa to the medieval towers of San Gimignano.
Beyond its cultural treasures, the Tuscan countryside reflects centuries of agricultural tradition, producing world-renowned red wines of the Chianti region and golden olive oil that have shaped the region’s economy and gastronomy for generations.
Learn More…
- Why cycle in Tuscany?
A bike tour is the perfect way to explore this enchanting landscape, combining gentle rides through vineyards and olive groves with stops in medieval towns and Renaissance cities.
Cyclists can enjoy a wine tasting tour in the Chianti hills, savor local cuisine, and pedal past sun-soaked fields that inspired centuries of painters.
For those seeking a more leisurely rhythm, a Tuscany bike and boat tour combines cycling with the comfort of evenings spent cruising Italy’s waterways, allowing you to immerse yourself in the region by both land and river.
- What are the highlights of Tuscany?
- Historic landmarks - Visit the Leaning Tower of Pisa, the walled towns of the Middle Ages & the medieval towers of San Gimignano
- Chianti region - Ride through rolling vineyards and olive groves, sampling world-renowned red wine, olive oil & enjoying a traditional wine tasting tour
- Tuscan countryside - Golden hills, sunflower fields & cypress-lined roads
- Cultural heritage - Explore towns and cities shaped by the Grand Duchy of Tuscany & the Renaissance
- Italian wine & cuisine - Indulge in Italy’s culinary heartland, pairing rustic dishes with exceptional wines
- Scenic variety - From the hills of Chianti to the coast of the Ligurian Sea
- When's the best time to visit Tuscany?
The best time to enjoy a Tuscany bike tour is spring (April–June) and fall (September–October), when the weather is warm but not too hot, and the Tuscan countryside is at its most colorful. In spring, fields bloom with wildflowers and cycling conditions are ideal, while the fall brings the grape harvest in the Chianti region, offering the chance to combine riding with a memorable wine tasting tour. Summer can also be a vibrant time to visit, with long sunny days, but it tends to be hotter and busier, especially in historic towns.
- Links for more information…
Cycling and Cooking in Tuscany
Italy 
Florence to Rome
Italy 
Tuscan Wine Classic: Pienza to Castellina via Siena
Italy 
Tuscany Getaway: 4 Nights in Siena, Montalcino & Pienza
Italy 
Tuscany and Umbria: Cycling in the Heart of Italy
Italy 
Tuscany's Legendary Gravel Routes
Italy 
Custom and Private Bike Tours in Italy
Italy 
Tuscany by E-Bike and Boat
Italy 
The best way to have an immersive experience in Tuscany
Tuscan Wine Classic: Pienza to Castellina via Siena
“The route, the bikes, the hotels. All received an A+ grade. Except the part of arriving in Pienza and leaving Castellina. The topic “How to get there”, part of a…” Full Review
“The route, the bikes, the hotels. All received an A+ grade. Except the part of arriving in Pienza and leaving Castellina. The topic “How to get there”, part of a e-mail sent by you should be improved. The option TAXI from Chiusi train station doesn’t exist. No taxis there. There is only one bus/day to Pienza that departures in the morning. And we arrived in the afternoon. After asking four different people we realized that the only way available would be to take a bus - a city bus, not prepared for the transport of passengers + luggage - to Montepulciano and then find a way to arrive in Pienza. We thought that we could take a taxi there. But no taxis either. Fortunately, cel phones were charged and with internet access, so we contacted the local operator, explained the situation and they went to “rescue us”.
The same uncertainty happened by the time we left Castellina. We had 4 bags (it was a 20 days vacation trip, with different activities, including a meeting in between - with a “social” dressing code). It would require a considerable effort to carry the luggage until the bus stop, to take another city bus until Siena and then find a way to go to Florence (the place where we would continue the trip). The lovely cities that we visited in Tuscany are in fact villages. There are no taxi services overthere.
Again, the tour operator helped us passing the contact of a private driver who led us from Castellina to Florence.
My suggestion: include the transfer to the starting point and from the finish point in the “to do list” for the local operators when cities have such a limited options of transportation.” Less
—Claudia Lutke
Loved it!!!
Tuscany and Umbria: Cycling in the Heart of Italy
“The biking was spectacular! We did the seven day tour but next time we would do the 9 day because there are more stops. Our guide Paolo was fantastic. The hotels were also great!!’”
—Rita S
Loved it!!!
Tuscany and Umbria: Cycling in the Heart of Italy
“The biking was spectacular! We did the seven day tour but next time we would do the 9 day because there are more stops. Paolo was fantastic. The hotels were also great!!’”
—Rita S
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