Siena - Tuscany

Italy

Siena - Tuscany, Italy

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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Photo Gallery

Via delle Querciole
The Palazzo Massaini in Pienza (Val d'Orcia)
View in Torre del Mangia, Siena

Best time to ride

Jan
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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.

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Where to stay

Base Towns

Gaiole in Chianti

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.

Agriturismo Il Molinello

Agriturismo Il Molinello

Asciano

From a mill in the XIV century to an agriturismo in 1996, Il Molinello ("little mill" in Italian) is located in a wonderfull place. In the lovely countryside of Asciano, it's the perfect spot to visit Tuscany and the Crete Senesi. They offer a full program of things to do for cyclists and non-cyclists.

Badia a Coltibuono

Badia a Coltibuono

Radda in Chianti

In the charming area of Badia a Coltibuono, this hotel is high level. It is a renovated farmhouse that now also hosts a winery and a restaurant. It is in the municipality of Gaiole in Chianti, not far from the start of L’Eroica.

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Cyclists riding together on a scenic road

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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)

Bicilettaio

Bicilettaio

Bike brands: Cinelli, Bianchi

In Gaiole in Chianti, Bicilettaio is a solid spot for high-quality road bikes. They're well set up for the local terrain and make it easy to get rolling. You can also rent pedals, accessories, and even bikepacking gear if you're going long.

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Shops (4)

La Bottega

La Bottega

La Bottega is a beautiful, artfully decorated shop that every road cycling fan will love. Inside you will find vintage pieces, great clothing, and details that bring cycling’s past to life. Friendly service and a warm atmosphere make it an easy place to linger or pick up a special souvenir.

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Cafes & bars (16)

Agribar Brolio

Agribar Brolio

Coming down from Brolio's Castle, you'll zip right past Agribar Brolio. Tap the brakes and pull in for a coffee or a drink. The place has that classic L’Eroica vibe, and it’s a great spot to soak it all in before rolling on.

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Road Cycling Routes (14)

Chianti West

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

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

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

Loop du France

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Loop du France

Loop du France

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Loop du France

Loop du France

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Map of Siena - Tuscany - 48 pins

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