The Best Cycling Routes in Sienna - Tuscany
Discover the best cycling routes in Sienna - Tuscany, Italy. Our curated collection includes 12 handpicked routes, from shorter coffee rides to challenging all-day rides. Each route includes GPX files, detailed elevation profiles, highlighted climbs, and recommended cafés stops along the way.
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12 routes
The beauty of Rapolano Terme
Rapolano Terme, the finish of stage six of the 2024 Giro d’Italia, is an ideal base for exploring this part of Tuscany. This route reaches Sinalunga, on the border with the province of Arezzo. The toughest climb follows the Lauretana road, scenic and quiet. Asciano and Serre di Rapolano are the final villages where you can experience a typical day in the Siena area.
San Gimignano, Volterra & Monteriggioni
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.
Eroica loop from Gaiole in Chianti
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
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.
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