Cycling day trip from Gaiole in Chianti to Siena

This ride takes you from the charming village of Gaiole in Chianti, right in the heart of Tuscany’s famous wine region, down to the stunning medieval city of Siena. It’s about 44 kilometers and mixes up plenty of road surfaces—expect a real taste of Tuscany with smooth asphalt, classic gravel sections (think L’Eroica style), and even a few cobblestone stretches to keep things interesting!

The rolling Chianti hills will give your legs a workout, with nearly 1,000 meters of climbing, but the incredible views of vineyards and olive groves are worth every pedal stroke. The route sticks mostly to quiet country roads and white gravel lanes, so you’ll enjoy plenty of peace and those iconic Tuscan vistas.

After some exhilarating descents and a bit of meandering, you’ll roll into Siena—a UNESCO World Heritage site, famous for its shell-shaped Piazza del Campo and the dramatic Duomo. If you’ve still got energy, reward yourself with a gelato in the square! This route is perfect for adventurous cyclists who want to soak up Tuscan culture from the saddle.