Road Cycling Routes near Montalcino

A loop route of great charm starting and ending in Buonconvento. It offers everything you could wish for in a road bike ride south of Siena: white roads, switchbacks, striking climbs and descents, unique landscapes. Along the way you pass through beautiful villages such as Castiglion del Bosco and Montalcino.

This ride through the Crete Senesi begins and ends in Montepulciano, known for one of Italy’s finest red wines. The first climb of the day leads to Pienza, whose historic center is a UNESCO World Heritage site. Through a beautiful sequence of hills, you return to Montepulciano via Bagno Vignoni, San Quirico d’Orcia, and Chianciano Terme.

Monte Amiata is one of the highest paved roads in Tuscany. It has many sides; this one is called “Gatto d’Oro” because it passes a restaurant with that name. In addition to this long and iconic climb, the highlights of the route are a lesser-known ascent to Montalcino and the beautiful town of Radicofani.

Of the two loop routes that make up the Strade Bianche pro race, this is the southern one. The climb to Montalcino is long and steady, while the following gravel section has a timeless appeal. The rolling route, lined with cypress trees that symbolize this part of Tuscany, passes Lucignano d’Asso. The final real climb back to Buonconvento, again on gravel, is Pieve a Salti.