Road Cycling Routes near Siena

Gaiole in Chianti is well known in the cycling world as the home of the Eroica. It is a historic reenactment of early cycling: for one day, thousands of riders use vintage bikes, wear 1920s-style clothing, and ride the dusty white roads. This route follows the opening and closing sections of the permanent Eroica course. The climb to Brolio Castle is especially beautiful.

A feast of Tuscan hills. The route passes some of the most iconic villages in the provinces of Siena and Pisa, including San Gimignano and Volterra. The climb to Volterra, about 8 kilometers at an average of 5%, is a perfect excuse for a proper Tuscan lunch.

Roughly 1/3 of this route is on gravel, which is nicely spread over the entire ride. In the southern part of the route you'll find some sections that are also included in the Strade Bianche race.

The most famous and noteworthy loop featuring white roads. It is part of the popular Gran Fondo Strade Bianche and includes some of the race’s most iconic sectors, such as San Martino in Grania, Colle Pinzuto, and Le Tolfe. The finale takes place on the iconic Via Santa Caterina, the brutal final wall where riders like Wout van Aert and Mathieu van der Poel, among others, have written history.

The classic finale of the well-known Strade Bianche cycling race. This route takes you onto some of the most iconic sections of the event, including the steep Bagnaia climb, the long Radi sector, and the final two sections, Colle Pinzuto and Le Tolfe. Here the gradients reach about 18% and the gravel roads become a demanding stretch of dust. You finish the route with clear impressions and lasting memories.