Cycling day trip from San Gimignano to Volterra

This route takes you from the iconic medieval towers of San Gimignano to the ancient hill town of Volterra—two jewels of Tuscany, just over 34 km apart. It’s a ride packed with both history and classic Tuscan landscapes!

Be ready for some real adventure: over half the ride rolls over unpaved ground and gravel—perfect if you love a little off-road action mixed with countryside tranquility. Tracks and quiet country roads dominate, winding through vineyards, olive groves, and forested hills. You’ll rack up a good amount of climbing (over 1100 meters ascent!), so bring plenty of water and your climbing legs.

San Gimignano is famous for its skyline of medieval towers, while Volterra is known for its Etruscan roots and impressive ancient walls. Between the two, you’ll experience hilltop vistas and timeless rural charm.

It’s not the easiest ride, but for seasoned cyclists with a taste for gravel and stunning views, it’ll be a Tuscan memory you won’t forget. Panninis at the finish, anyone?