Cycling day trip from Siena to San Gimignano

Get ready for a classic Tuscan ride! Starting in the medieval heart of Siena, you’ll weave your way north across rolling countryside, charming villages, and plenty of those famous cypress-lined roads. The first stretch is a bit demanding with over a thousand meters of climbing, but the breathtaking views of olive groves and vineyards more than make up for it. About half the ride is on good, paved roads, but expect a fair share of gravel and unpaved sections—nothing too technical, but you’ll want sturdy tires and a sense of adventure (hello, Strade Bianche vibes!).

Your finish line is San Gimignano, the “Medieval Manhattan” with its signature towers rising dramatically above vineyards. Once you roll in, park your bike in the historic center and reward yourself with some gelato (the world-champion shop is right on the main square). This route is all about soaking up classic Tuscany: intense climbs, quiet roads, sweeping views, and towns bursting with history at both ends. Enjoy the ride!