Cycling day trip from Greve in Chianti to Siena

Get ready for a ride that captures the magic of Tuscany! Starting in Greve in Chianti, famed for its wine, olive oil, and charming medieval square, you’ll roll south through some of the region’s most iconic scenery. The route is about 73 km, mostly along quiet roads with a good mix of classic Tuscan asphalt and a bit of gravel to add to the adventure. You’ll climb and descend nearly 1,800 meters as you wind through hilltop villages, rows of cypress trees, and endless vineyards.

Give yourself plenty of time to soak in the views (and maybe stop for a mid-ride espresso). The route isn’t flat, but the breathtaking panoramas and peaceful country lanes make every climb worthwhile.

You’ll end in Siena, famous for its stunning shell-shaped Piazza del Campo and spectacular Duomo—a perfect spot to rest your legs and celebrate the ride. Whether you’re here for the challenge, the landscapes, or the culture, this route between Greve in Chianti and Siena is pure Tuscan gold.