Siena - Tuscany
A popular song calls Siena “the city of dreams and chimeras.” Divided into 17 contrade, it is certainly one of Italy’s most unique cities. Its sloping Piazza del Campo hosts a famous horse Palio twice a year. Across much of the province, the hills are irresistibly beautiful.
From Siena, road cycling can take you to the sea or lakes, on long or short climbs, on asphalt or gravel. A true paradise for two wheels, Siena offers everything a lover, not just for cycling, but of good living, could wish for.
Some of the climbs around Siena became famous worldwide thanks to events such as the Strade Bianche pro race or the Eroica old-school event: Monteaperti, Le Tolfe or Via Santa Caterina are everything you need from a cycling point of view.
Italian writer Mario Luzi used to say: "Being in Siena, always, excites me a little, almost like it gets me drunk." And it's not just because the city and its countryside offer some of the very best wines in Italy. The culture, the landscapes and the arts are such an overwhelming presence around you.
And the food is great as well: Tuscany has some of the best meat and pasta in the entire country. In the most positive way, a cycling trip to Tuscany will stay with you forever.
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Best time to ride
Siena's hills are a true wonder for most of the year. If you can, skip the coldest stretch in December and January and the peak heat of July and August to keep riding simple and comfortable. There’s a reason the area’s most celebrated road cycling events land where they do. Strade Bianche rolls out in early March, and L’Eroica follows in early October, right when the conditions feel just right.
Where to stay
Base Towns
Gaiole in Chianti
One of the best-known places north of Siena and a Chianti hub, often nicknamed "Chiantishire". Gaiole is the starting point of L’Eroica, the famous vintage cycling event. Some of Italy’s most famous hills and views are near Gaiole, making it ideal for a legendary holiday.
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Accommodations (8)
Places in Siena - Tuscany that welcome you and your bike.
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How to get there
- By car: Via the A1 highway, then several beltways get you closer and closer to Siena. Because of its hills, it's not super easy to get there.
- By train: Siena's stations are reachable from Florence or Rome, but it's quite a long journey. If you bring your bike always check if the train opperator allows bikes on the train. An additional ticket for your bike might be needed.
- By plane: The closest internationl airports are Florence (FLR - 55 kms away) and Pisa (PSA -ndfsanB. K 85 kms away). From either airport you can quickly reach a train station that heads towards Siena.
Bike Rentals (8)
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Shops (4)
Cafes & bars (16)
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Popular Climbs (12)
Road Cycling Routes (14)
Chianti West
48.7 km | 979 m | Moderate
Loop around the Chianti area, that shows you all the beauty of the region while you ride on tarmac. This route is fully paved, no gravel section. For a little detour you can add in the Brolio's Castle (gravel) when you pass through La Madonna.
Exploring Val di Merse
74 km | 1234 m | Moderate
The Val di Merse is considered a hidden gem in the area south of Siena. Starting from Casciano, the first stop is the San Galgano Abbey, a true highlight. The route continues with gentle climbs and descents along secondary roads and nature reserves, offering constant natural scenery.
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.
Loop du France
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Loop du France
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Loop du France
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