The beauty of fatigue and the thrill of conquest

The great adventure of L’Eroica is no longer restricted to the first Sunday of October but can be enjoyed all year long riding on the permanent route.

The permanent route, marked with permanent signs, covers 209 km through the heart of the Terre di Siena, crossing the Chianti, the Crete Senesi and the Val d’Orcia, completing a journey into the artistic essence of the legendary Tuscan countryside.

The route can be completed with all kinds of bicycles, even electric.”


L’Eroica and Anima Toscana offers the opportunity to get the road book kit to complete the permanent route of L’Eroica on your own.

You can obtain the “Road book kit” by regular mail to your home at the price of 10 euro, cost of delivery included, sending a request by e-mail to [email protected] The Kit includes:

  • Road book where you can post the stamp of each area of control on the permanent route
  • Map of the route
  • List of the authorized sites to post the stamp
  • Informations of the permanent route.


Anima Toscana offers travel solutions to complete the permanent route in 3, 4 or 5 days, or make custom packages following your needs, based on the days at your disposal or depending on the distance you want to cover by day.

For more information LOOK AT THE PACKAGES or send an email to [email protected] to receive a free offer.



The Eroica route starts in Gaiole in Chianti, winding among historical vineyards that lead you to Castello di Brolio with its cypress-lined entrance. The breath-taking panorama below the walls, over the vineyards, represents one of the most wonderful parts of the permanent route.

After a few kilometers, near San Giovanni a Cerreto, Siena will appear on the horizon. The visit to this wonderful medieval city with its Dome, Piazza del Campo and the perfect medieval city center will make your trip special.Technical characteristics: easy segment of 20 km, the only uphill climb is to reach Brolio Castle. After 10 km you will travel on an unpaved road for the first time on the trip. We urge extreme caution on this kind of road and that you move at your own pace.


Neat vineyards evolve into a more varied landscape, painted with the traditional Terra di Siena colours. Soon after leaving the city of Siena you’ll ride through a very typical segment of the route, located between “Colle Malamerenda” and Radi, deep in the gentle hills of Siena, studded with farm houses and medieval villages, merging your ride with the Via Francigena itinerary. Views of the village of Murlo will be the backdrop of the easiest segment of the whole permanent route. Technical characteristics: long segment of 47 km, the area around Siena is a mix of easy paved and unpaved roads. After Siena you will ride for 2 km on the busy Cassia road before reaching a long segment of unpaved roads, approximately 12 km long, which is composed of short steep climbs after the small town of Radi. We suggest refilling your water bottle in Vescovado before heading to Montalcino.


Climbing Castiglion del Bosco, one of the most challenging segments of the L’Eroica permanent route, you will reach Montalcino, which sits over the beautiful and panoramic lands of the home of Brunello of Montalcino. Montalcino, also famous for olive oil and honey, is a nice village that merits a visit, even just to admire the incredible views over the Val d’Orcia area. Technical characteristics: the segment from Bibbiano to Montalcino is one of the most difficult on the path. Passing the golf course of Castiglion del Bosco, you will ride a long and irregular climb, with slopes over 15%, surrounded by woods and vineyards.


The descent from Montalcino will be a devine dive into the vineyards, bringing you through smooth, pristine hills until Lucignano d’Asso, where you can take a rest with a typical snack or just to refill your water bottle. Riding in the landscape of the Val d'Orcia is a privilege for the eyes and mind that revives you, despite the strain of constant hills. Technical characteristics: the Val d’Orcia area includes 26 km of unpaved roads, sometimes challenging, out of a total of 30 km expected in this segment. Be careful around Lucignano d’Asso where you can meet livestock guardian dogs stay with the group of animals they protect as a full-time member of the flock.


From the vineyards and rolling hills to the beauty of the lunar landscape is a short step. Once you have left the villages along the Cassia, you will be immersed in the Crete Senesi with its characteristic gullies. Oak trees and cypresses indicate isolated farms where they produce cheese, and tables are enriched by the “diamond of the Crete Senesi”: the white truffle. This part of the route includes the difficult unpaved road of Monte Sante Marie, a very famous steep road that will take you back to the Chianti area. Technical characteristics: the road after Pieve a Salti will make it easier till you reach Caggiolo, where a difficult unpaved sector will begin, due to the bad road surface and slope. Once you have arrived at Asciano cemetery, we suggest a quick stop in Asciano town center to refill bottles before riding the long and very challenging road of Monte Sante Marie.

Route info