Cycling day trip from Siena to Montepulciano

Get ready for a classic Tuscany ride! Starting out from Siena—famous for its stunning medieval cityscape and the thrilling Palio horse race—you’ll twist and climb your way toward Montepulciano, a hilltop town renowned for its Vino Nobile wine and gorgeous Renaissance architecture.

This roughly 80 km route winds through rolling hills and charming landscapes, with over 1,500 meters of climbing. You’ll be treated to a true mix of surfaces—expect everything from smooth paved stretches and quiet tarmac to plenty of gravel and loose tracks (over half the ride is unpaved!), so wider tires are your friend. The route mostly follows quiet backroads and tracks, meaning you can soak in the Tuscan countryside without too much worry about traffic.

You’ll pass by olive groves, sunflower fields, and maybe even catch a glimpse of those iconic cypress-lined lanes. The final ascent into Montepulciano is a proper leg-tester, but the reward is one of Tuscany’s prettiest towns—perfect for a well-earned gelato or glass of wine on a sunny piazza. Buon viaggio!