Total tour distance: 193 miles
Daily tour distance: 32 miles
Difficulty: 50 / 100
Food, wine, romance, culture, art and more romance. What else could be on your wish list for a Tuscany cycling tour? Every town has its own rich history and secrets for you and your loved ones to discover. And the food… oh the food. Even the most low-key restaurants have the most delectable food.
All of our tours begin in Florence and hit well-known areas within the region: Panzano, San Gimignano, and Siena. Longer tours include rides and stays in Montepulciano, Montalcino, and the Umbrian village, Castiglione del Lago.
If you have a week to discover Tuscany, we have the tour for you. Even with less than a week to spare, you will find yourself cycling along some of the most scenic roads in the world, sipping cappuccino in the mornings, sampling fine Chianti in the afternoon, and savoring sumptuous regional foods by night. The lauded natural beauty and romantic scenes of Tuscany have not been overstated. What better combination for a romantic getaway or family vacation? Come and discover Tuscany for yourself with our 6-night bicycle vacation!
Day 1: Florence to Panzano – 49km
Our guide will meet you in the morning at our bike rental shop in the heart of Florence. After being fitted properly, you will hit the road! Navigate the busy Florence streets during the early hours of your tour; once you leave the city, enjoy a lovely 49km to ride Panzano. After checking in to your hotel, you will have time to relax, refresh yourself, and explore the town. Your luggage will be there when you arrive, so feel free to enjoy the pool and try the local Chianti before dinner. Dinner is included tonight.
Day 2: Panzano to San Gimignano 41km
Your second day in Tuscany day centers around a 50km ride along small, rolling back roads to San Gimignano, the city of towers. Add on an additional 20km if you want a bit more time in the saddle. Our historic hotel is right in the middle of the old town. Dinner is included tonight.
Day 3: San Gimignano to Siena – 59km
A glorious 70km ride of traffic-free backcountry roads is in store for you today, with your journey culminating in Siena. A beautiful, small city, Siena is at the heart of the region. Dinner is on your own tonight, so enjoy exploring the old city in search of all the culinary delights Siena can offer. Our hotel is inside the town gates and perfectly situated for easy exploration of Siena and the surrounding areas.
Day 4: Siena to Montepulciano via Montalcino – 89km
Exit Siena the way you came in on small back roads with grand views of the city. Head South on rolling roads to another small, historic hilltop town—Montalcino, the home of the famous Brunello wines. After a brief exploration of Montalcino, ride another 40km to Montepulciano, where you will stay in a beautifully-restored farmhouse that is owned by a family of wine exporters and experts. They are available to coordinate special tours and tastings, and even to host a class on how to cook an authentic Tuscan meal! We recommend dinner here both nights. The cooking school is not included in the price – so let us know in advance if you want this arranged. If you opt out, you are on your own for dinner, and there are many fine restaurants in the area.
Day 5: Montepulciano and Pienza loop – 34km
Today’s lovely loop ride option gives you the opportunity to explore Pienza [what is in Pienza? We need a bit more here]. The journey is 34km round trip, and hilly. En route to Pienza, take the time to stop in Monticchiello, another special hill top village. A great route if you are feeling adventurous, or just want a good ride.
Day 6: Montepulciano to Castiglione del Lago – 30km
Head into Umbria today, to Lake Trasimeno, where you will stay in the lovely village of Castiglione del Lago. The 44km ride from Montepulciano to Castiglione del Lago is easy and quick, which allows more time in either your start or finish town. Castiglione del Lago is perched on a promontory, overlooking the lake. The hotel is in the historic part of Castigliano, which is full of interesting sites and shopping. Dinner is included.
Day 7: Castiglione del Lago to Florence
Depart for Florence by cycling to the train depot and catching the 10:00am train**. The Florence train station is within a few blocks of our bike rental shop where the tour ends. Earlier trains are available and it would be possible to catch an evening flight. Also, we have several recommendations for hotels near the bike shop and at the airport.