Sienna - 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 of 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, Siena will stay with you forever.
Photo Gallery
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.
Preview Content
Unlock the full guide
Preview Content
Unlock the full guide
Accommodations (8)
Places in Sienna - Tuscany that welcome you and your bike.
Agriturismo Il Molinello
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
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.
Preview Content
Unlock the full guide
Preview Content
Unlock the full guide
Preview Content
Unlock the full guide
Get full access to the Ride Atlas
Buy the Sienna - Tuscany Guide and 15 other guides for a one-time fee of just €29.95. That's only €1.87 per guide
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
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.
Preview Content
Bike brands: Premium Brands Available
Unlock the full guide
Preview Content
Bike brands: Premium Brands Available
Unlock the full guide
Preview Content
Bike brands: Premium Brands Available
Unlock the full guide
Get full access to the Ride Atlas
Buy the Sienna - Tuscany Guide and 15 other guides for a one-time fee of just €29.95. That's only €1.87 per guide
Shops (4)
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.
Preview Content
Unlock the full guide
Preview Content
Unlock the full guide
Preview Content
Unlock the full guide
Cafes & bars (16)
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.
Preview Content
Unlock the full guide
Preview Content
Unlock the full guide
Preview Content
Unlock the full guide
Preview Content
Unlock the full guide
Get full access to the Ride Atlas
Buy the Sienna - Tuscany Guide and 15 other guides for a one-time fee of just €29.95. That's only €1.87 per guide
Popular Climbs (12)
Brolio's Castle
750m | 65m | 8.7%
The first real climb of L’Eroica. It is often tackled while it is still dark and with candles in hand. It is beautiful and short, but the gradients make themselves felt. It is one of the most famous white roads in the province of Siena.
Colle Pinzuto
2.16km | 99m | 4.6%
Colle Pinzuto is one of the final gravel sectors of the iconic professional March race. It features a steep dirt wall at the start, while the top levels out noticeably. A right-hand hairpin is particularly tough and can be slippery.
Preview Content
m | m | %
Unlock the full guide
Preview Content
m | m | %
Unlock the full guide
Preview Content
m | m | %
Unlock the full guide
Cycling Routes (12)
The beauty of Rapolano Terme
48.3km | 542m | Easy
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
131.2km | 2076m | 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.
Eroica loop from Gaiole in Chianti
51.5km | 868m | 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
km | m
Unlock the full guide
Loop du France
km | m
Unlock the full guide
Loop du France
km | m
Unlock the full guide
Map of Sienna - Tuscany - 48 pins
Unlock the full guide
Get the complete guide with all routes, climbs, and local tips for Sienna - Tuscany
Already have an account? Log inCommunity Discussion
Join the conversation, ask a question or share insights about Sienna - Tuscany.
No questions yet
Be the first to ask the community about cycling in Sienna - Tuscany!
Reviews
Write a review Write a reviewNo reviews yet
Be the first to share your experience about riding in Sienna - Tuscany!
