Permanent route of L'Eroica

Area 1 - CHIANTI Going

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.


You will return to the Chianti area through Castelnuovo Berardenga, the village on the border with the Crete Senesi. After the panoramic descent to Pianella, the road to Radda in Chianti will be a sequence of vineyards and woods, passing through pretty villages and farms, that could offer you a wide range of local produce such as, wine and olive oil tasting, temptations that will delight your itinerary and your senses. After Radda in Chianti you’ll head to Gaiole, the beginning and the end of your experience, riding through Vertine, a nice little pearl. Technical characteristics: Castelnuovo Berardenga and the next part of road will allow you to relax after the effort on Monte Sante Marie. After Pianella you climb the long gravel road to Radda in Chianti, which is 500 meters above sea level, before you descent to Gaiole in Chianti.


The Eroica and Soul Tuscany offer , to those who want to , can get the kit to be able to face the permanent path in total freedom . You can apply for a " road book " kit by mail at a cost of 10 Euros , postage included , send an email to , followed by a reply email which will be indicated on the payment method .
The kit consists of :

  • Road book in paper format where to affix the stamps that certify the completion of the course ;
  • Route map ;
  • List of acceptance to the issuance of stamps;
  • Information note on the course.


Once the road book with six validation stamps , you can apply for the Award of " Heroic " personalized with your own name, at a cost of 15 Euros ( postage included) . In order to receive the diploma you will need to scan the road book and send the scan to , once verified the completion of the route via the affixed stamps , you will receive personalized certificate directly to your home .

* You can request the complete kit " Road Book + Certificate " at a cost of 22 Euros , postage included .


Do you want an all inclusive service

Want one more service ?
Soul Tuscany will organize , for every weekend from April to November, a collective baggage collection along the Permanent Path , for those wishing to travel solo but with a few extra amenities . The cost for each route is :

  • 25 € for Heroic " solo " ;
  • 40 € for two people ;
  • 15 Euros per person for groups of 3 to 8 people ;
  • 10 Euros per person for groups of 8 people .

“If you want to travel without worries, Eroica Travel by Anima Toscana proposes many travel solutions, customized too, to ride the Permanent Route in 3 or more stages, providing all services a cyclist could require. For more information, visit the website or send an email to “





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