Tuscan Hill Towns by Bike
Experienced cyclists thrill to Tuscany’s famous hills—but you don’t have to be a cyclist at all to fall under the spell of this enchanting region. Here, you’ll find a countryside whose beauty is rivaled only by the fabulous paintings and frescoes that abound in villas, churches, and museums … ancient cities that helped shape the course of civilization … and a hearty cuisine coupled with world-class wines. From San Gimignano, bristling with medieval towers, to Gothic Siena, a model of early urban planning, you’ll explore the heart of this region, enjoying special touches like wine tastings and a lecture by a local historian along the way.
- Cycle through the classic rolling Crete Senesi hills
- View the 13 towers of medieval San Gimignano
- Sip local vintages at the Vernaccia Wine Museum
- Master Italian phrases, courtesy of your Trip Leaders
- Hear a lecture on the Renaissance by a local art historian
- Admire Gothic Siena, a UNESCO World Heritage Site
- Explore Siena’s historic contrade neigborhoods
- Enjoy a Tuscan picnic lunch outside Montepulciano
- Taste Tuscan wines at a renowned Pienza enoteca
- See the Orcia Valley, a UNESCO World Heritage Site
What to Expect
This tour offers the full range of easy terrain mixed with moderate and challenging hills. Our VBT van support shuttle is always available for those who need assistance with the hills. Ideal for more experienced cyclists.
Average Daily Mileage: 15-45 miles (24.1–72.4 km)
Average Daily Cycling Time: 3-5 hours
Average High/Low Temperature (°F) – Florence
Apr 68º/46º May 75º/53º Jun 84º/58º Sep 81º/58º Oct 69º/51º
Average Precipitation (in.) – Florence
Apr 2.9 May 3.0 Jun 2.7 Sep 3.3 Oct 4.0
E-Bikes Available on this tour.
Limited quantities — first come, first serve. Learn more.
Bicycle Vacation Only – without Air
- 6 nights in 4-star historic hotels and one country villa
- 10 meals – 6 breakfasts, 1 lunch, 3 dinners
Air Package Plus
- Roundtrip international airfare
- 8 nights in 4-star historic hotels and one country villa
- 12 meals – 8 breakfasts, 1 lunch, 3 dinners
- Airport transfers
- And the option to add our Low-Cost Trip Extensions: Pre-trip: Florence – 2 nights for only $345* • Post-trip: Rome – 2 nights for only $345
Both Vacation Options Include
- FREE use of our custom VBT bicycle and helmet — New E-Bikes available
- Service of two bilingual VBT Trip Leaders
- FULL VAN SUPPORT
- Daily route directions and maps
- Welcome reception with local wine and hors d’oeuvres
- Sightseeing and cultural activities
- 5% Frequent Traveler Credit to use on your next VBT vacation
- Special Good Buy Discount
Fuji Gran Fondo
For more info see our VBT Bikes page.
Click here to download our Suggested Reading List.