Total tour distance: 230 miles
Daily tour distance: 30 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 10-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 Rest Day or Volterra Loop – 60km
You can take a day off of the bike to rest, shop, and explore San Gimignano, or instead ride the beautiful 60km loop to Volterra. One of the many famous hilltop towns of Tuscany, Volterra is full of fine shops and features a museum. Dinner is on your own tonight.
Day 4: 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 5: Siena Exploration
Today is a day off the bike, one designed to allow you to fully explore the historic sites and do some gift shopping. [Can we say more about what there is to see in Siena?] Dinner is again on your own tonight so keep your eyes peeled for the best option.
Day 6: Siena to Montalcino – 50km
Exit Siena the way you came in, on small back roads with grand views of the city. Head South on 50km of rolling roads to another small, historic hilltop town—Montalcino, the home of the famous Brunello wines. You are on your own for dinner, and there are many fine options to select from.
Day 7: Montalcino to Montepulciano – 40km
You depart Montalcino to start an eventful day. The direct route is to Montepulciano is only 40km, but several options (some with hills) give you a chance to add as much mileage as you would like. Included along your ride is a stop in the town of Pienza, a great place for lunch and exploration. In Montepulciano, 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.D
ay 8: Montepulciano Exploration
You can walk to Montepulciano or cycle there and spend the day exploring this gem. It is your day to discover and enjoy. Dinner is on your own, including the possibility of taking the class at your hotel!
Day 9: Montepulciano to Cortona via Castiglione del Lago – 44km
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, and an excellent lunch stop. Cortona is another gem. Hotel Villa Marsili is in the heart of the town to allow easy exploration on your last day. Since it has no restaurant, you get to explore this wonderful village in search of an ideal dinner spot. Ask about Il Falconiere – it has a Michelin Star and is in the hills above town.
Day 10: Cortona Exploration and Monte Petrano
What you do today is up to you—hit the road on your bike or explore the town. There are some beautiful rides in the area (the 2009 Giro had a mountain top finish at Monte Petrano, which is not too far from Cortona). However, a day in town might be spent exploring the narrow steep streets and enjoying the medieval architecture. Dinner is not included.
Day 11: Cortona to Firenze
Depart for Florence by cycling to the Cortona train station and catching a morning 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.