Cycling day trip from Siena to Greve in Chianti

This route takes you from the medieval brick wonders of Siena to the heart of Chianti wine country, ending in charming Greve in Chianti. Leaving behind Siena’s famous Piazza del Campo, you’ll wind your way north for just over 74 km on a mix of quiet roads, tracks, and some classic Tuscan gravel—perfect for a taste of the famed strade bianche. With over 1,700 meters of climbing, get ready for rolling hills, cypress-lined vistas, and more than a few great photo ops.

The ride is mostly on paved or quiet rural roads, but don’t be surprised by the occasional stretch of gravel or unpaved lane—this is Tuscany, after all! Ancient vineyards and small villages dot your route. Once you reach Greve in Chianti, reward yourself with a glass of local wine in the bustling main piazza, surrounded by arcades and wine shops. Whether you’re chasing miles or just savoring the landscape, this ride is classic Tuscany at its best!