Cycling day trip from Monteriggioni to Siena

This route takes you from the medieval walled town of Monteriggioni to the lively city of Siena—a classic ride through the heart of Tuscany! Starting at Monteriggioni, famous for its perfectly preserved towers and walls dating back to the 13th century, you’ll roll out on mostly paved roads, and enjoy a peaceful ride with just a few busy sections.

The route is about 20 km long and packs in nearly 500 meters of ascent, so get ready for some rolling hills (and those classic Tuscan views!). While most of the path is smooth asphalt, keep an eye out for a few stretches with cobblestones and gravel, especially as you near Siena.

You’ll pass through quiet country roads and charming landscapes, then finish in Siena, known for its beautiful Piazza del Campo and the historic Palio horse race. Perfect for a half-day ride with plenty of photo stops! Just bring a little extra water—and maybe a camera for those hilltop views.