Cycling day trip from Siena to Montalcino

Get ready for a classic Tuscan bike adventure from Siena to Montalcino! Starting in the heart of medieval Siena—famous for its stunning Piazza del Campo and its annual Palio horse race—you’ll pedal south through rolling hills, cypress-lined roads, and postcard-worthy vineyards. The route covers about 50 km and is a spicy mix: roughly half paved and half unpaved, including plenty of traditional gravel (strade bianche), so a gravel or sturdy hybrid bike is your best friend.

Expect a good amount of climbing (almost 900 meters of ascent!), but the effort pays off with sweeping views of the Val d’Orcia. There’s barely any busy road, so you’ll mostly enjoy peace and quiet on quiet backroads and classic Tuscan tracks.

Your finish line is the hilltop town of Montalcino, home of the world-renowned Brunello wine. Treat yourself to a glass and soak in the panorama—you’ve earned it! This is a real taste of Tuscany, blending history, scenery, and a little “gravel grind” adventure.