Cycling day trip from San Gimignano to Siena

Get ready for a classic Tuscan ride from the medieval towers of San Gimignano to the historic heart of Siena! This roughly 56 km journey takes you through rolling hills, vineyards, and some seriously postcard-worthy countryside. You’re in for a good workout, too—expect over 1,200 meters of climbing along the way.

The route is a mixed bag surface-wise: you’ll spend about half the ride on smooth paved and asphalt roads, but also get a true taste of Tuscany’s white gravel roads—the famous “strade bianche.” There’s some cobblestone and loose gravel, so wider tires are your friend!

San Gimignano is a UNESCO World Heritage site, known for its dramatic towers and delicious gelato (fuel up before you go!). As you roll towards Siena, the landscape just keeps delivering those classic cypress-dotted vistas. Finish your ride by gliding into Siena’s iconic Piazza del Campo, home of the legendary Palio horse race. In short: challenging but unforgettable, with epic Italian charm the whole way.