Road Cycling Routes near Siena
Discover the best road cycling routes near Siena in Siena - Tuscany, Italy. We've curated 6 road cycling routes within riding distance of Siena. The area offers hilly terrain. Each route includes GPX files, detailed elevation profiles, highlighted climbs, and recommended café stops along the way.
6 routes
San Gimignano, Volterra & Monteriggioni
131.2 km • 2076 m • Hard
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.
Southern Chianti
76.1 km • 1422 m • Moderate
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.
Eroica loop from Gaiole in Chianti
51.5 km • 868 m • Moderate
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.
Medio Fondo Strade Bianche
84.6 km • 1134 m • Moderate
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.
Crete Senesi loop ft. Monte Sante Marie
61.4 km • 987 m • Moderate
Monteroni d’Arbia is the gateway to one of the most iconic sectors of the Strade Bianche: San Martino in Grania. Due to its length and elevation profile, it is considered the most difficult. Only Monte Sante Marie, where Tadej Pogačar attacked two times to win the race, is tougher, and you ride that as well today. Monte Sante Marie starts near the Asciano cemetery and ends only at Torre a Castello. After Castelnuovo Berardenga and Monteaperti, you return to Monteroni via a final gravel sector.
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