Italy 5-Day Biking Tours & Itineraries

Explore 2 biking trips designed by local kimkim specialists to get ideas for your trip to Italy.

If you have 5 days to explore Italy by bike, consider one of our carefully crafted itineraries to enrich your adventure. Explore Tuscany on a cycling route similar to this cycling Tuscany trip, which takes you from Florence to Siena and offers an adventurous ride through the region's famed wine country, medieval villages, and historical sites. Alternatively, you might prefer something like this bike journey from San Gimignano to Murlo, where the rolling hills, ancient towers, and the opportunity to taste Brunello wines present a different view of Tuscany's rolling landscape and rich cultural history. 

See more Italy Biking Tours & Itineraries.

Plan your trip to Italy
Chat with a local specialist who can help organize your trip.
Bicycles are a great way to get around Florence and the surrounding region
Map of Cycling Tuscany: Florence to Siena - 5 Days
Cycling Tuscany: Florence to Siena - 5 Days

Take a quick spin through the birthplace of the Italian Renaissance with this five-day Tuscan cycling tour. This challenging bike route will take you through the medieval villages and cypress-spotted hills of the Tuscan wine region . Go from Florence to Siena as you take in the region's food, historic castles, and sun-kissed landscapes, accompanied, of course, by a good glass or two.

Cycle through the scenic Tuscan countryside
Map of Tuscany By Bike: San Gimignano, Siena & Murlo - 5 Days
Tuscany By Bike: San Gimignano, Siena & Murlo - 5 Days

Tuscany is famous for its beautiful landscapes, vineyards, cypress trees, farms, and medieval hill towns. What better way to experience some of the best views in Italy than by bike? With this brief but immersive five-day itinerary, you'll explore the hills and towers of San Gimignano, have a chance to taste Brunello wines in Montalcino, and learn about the history and architecture of Siena.