Cycling day trip from Montalcino to Siena

Roll out from hilltop Montalcino, famous for Brunello di Montalcino and its 14th‑century fortress, and drop onto cypress-lined lanes and classic strade bianche. It’s about 50 km with a net downhill (roughly 690 m up, 920 m down), mixing quiet roads and farm tracks. Roughly half the route is unpaved, with long stretches of gravel and some loose sections, plus a few short links on busier roads.

You’ll glide through the Val d’Orcia vineyards toward Buonconvento (handy coffee and water stop), then traverse the rolling clay ridges of the Crete Senesi en route to Siena. The white roads here echo the famed Strade Bianche race that finishes in town.

Aim for wide tires (35–40 mm), carry a spare tube, and bring lights for the brief trafficier bits. Expect big views, olive groves, and the occasional punchy ramp.

Finish in Siena, a UNESCO-listed gem with the shell-shaped Piazza del Campo and the striking black-and-white Duomo. Toast the ride with a gelato or a glass of local vino before wandering the medieval lanes.