With Terra Eroica, the province of Siena becomes a cycling paradise


The “Northern Classics” are back and, with them, the desire among cycling enthusiasts to jump onto their saddles and ride in the pleasant spring temperatures. Easter is also fast approaching, bringing with it a few extra days of vacation. So, why not take this opportunity to cycle in the magnificent countryside of the province of Siena? Or rather in Terra Eroica, the Permanent Routes of L’Eroica and Eroica Montalcino?

So don’t delay! Map in hand, here are the proposals for cycling around Terra Eroica, a land which is inextricably linked to three events of great international interest: L’Eroica, Eroica Montalcino, and Nova Eroica Buonconvento. Three cycling proposals (www.eroica.cc), for every type of cyclist and every type of bicycle; from e-bikes to muscle-powered gravel and vintage bikes. Consider this an invitation to the Terra Eroica alone or in the company of friends, family, or teammates.

With Terra Eroica, the province of Siena becomes a cycling paradise
Terra Eroica – foto Guido Rubino

Here are the Terra Eroica proposals in detail

L’Eroica Permanent Route

AREA 1: the CHIANTI Valley – km 36

The first part of the route takes you up the gentle climb to one of the most beautiful symbols of the Chianti region and of L’Eroica, Brolio Castle. The cypress-lined road leading up to the castle, the section that runs by its walls and the descent to breath-taking panoramas and vineyards, represent one of the most beautiful sections along the permanent route.

Before tackling one of the best sections of white road along the route, a short detour will take you into one of the most beautiful medieval cities in the world: Siena, with its Cathedral, Piazza del Campo and the amazing historical centre.

Technical characteristics: relatively easy 20 km segment, during which the only long uphill climb is to Brolio Castle. On the way down from the castle you will have your first experience on gravel roads (2 km) and we suggest that you proceed with caution, considering that the descent is very steep in places.


Neat cultivations of wheat, grass and sunflowers evolve into a more varied landscape, painted with the traditional Terra di Siena terracotta 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 farmhouses and medieval villages, your ride merging with the Via Francigena route. Views of the village of Murlo will be the backdrop to one of the easiest segments of the whole route, in terms of elevation.

Technical characteristics: long 47 km segment, the area around Siena is a mix of easy hills, with short sections of gravel roads. After Siena you will ride on the busy Cassia road for 2 km before reaching a long 12 km segment of gravel road, which is composed of short steep climbs after the small town of Radi. We suggest that you have something to eat and drink in Vescovado before heading on to Montalcino.

Terra Eroica – foto Davide Mazzocco


Castiglion del Bosco, one of the most challenging segments of white road, made famous by the legendary stage of the Giro d’Italia in 2010, you will find yourselves on the beautiful and panoramic hills that produce Brunello di Montalcino wine. Montalcino, also famous for its olive oil, honey and organic produce, is a charming town 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 whole route. Passing the golf course at Castiglion del Bosco, you will face a long climb that is almost completely on white roads, surrounded by Mediterranean scrub. Climbs are irregular and often exceed 15% gradient.


The descent from Montalcino first involves a delicious dive into vineyards, then takes you through smooth, pristine hills until Lucignano d’Asso, where you can take a break with a typical Tuscan snack or just to refill your water bottle. Riding through the Val d’Orcia is a refreshing treat for the eyes and the mind, despite the strain of constant hills. The town of Buonconvento is a delight.
Technical characteristics: the Val d’Orcia area involves 26 km of steep gravel roads out of a total of 30 km to be covered. Be careful around Lucignano d’Asso where you may come across sheepdogs guarding their flocks.

Terra Eroica- foto Guido Rubino


From vineyards and rolling hills to the stark beauty of a lunar landscape is a short step. Once you leave the villages along the Cassia, you will be immersed in the Crete Senesi with its characteristic hills and gullies. Oak trees and cypresses indicate isolated farms where cheese is produced, and the local cuisine is enriched by the “diamond of the Crete Senesi”: the white truffle. This part of the route includes the difficult gravel road of Monte Sante Marie, the infamous steep hill that will take you back to the Chianti area.

The most difficult climbs on the entire route, reaching up to 20% gradient, are found in is section. The climbs are repetitive but are not particularly long.

Technical characteristics: after Pieve a Salti the route becomes easier until you reach Caggiolo, where a difficult gravel section begins, due to the bad road surface and the slope. Once you arrive at Asciano cemetery, we suggest a quick stop in Asciano town centre to refill bottles before riding the long and very challenging Monte Sante Marie segment.


Return to the Chianti area through Castelnuovo Berardenga, the village on the border with the Crete Senesi. The road to Pianella presents a sort of summary of the varied scenery that you have seen and will see while riding L’Eroica. The long road that climbs softly to Vagliagli and then on to Radda in Chianti passes a series of vineyards and woods, before the final unforgettable descent to Gaiole, riding through the perfect hamlet of Vertine.

Technical characteristics: Castelnuovo Berardenga and the next part of asphalt road will allow you to relax after the effort on Monte Sante Marie, before tackling the climb to Vagliagli along white roads. This last section, which is mostly along gravel roads, will take you to Radda in Chianti, 500 metres above sea level, before enjoying the final views on the descent to Gaiole in Chianti.

Terra Eroica – foto Davide Mazzocco


Once the road book has been completed with six validation stamps, you can request the “Eroica” diploma, personalized with your own name, at a cost of €15 (postage included). In order to receive the diploma, scan the road book and send the copy to info@animatoscana.it. Once the completion of the route has been verified via the affixed stamps, you will receive a personalized certificate directly to your home.
*You can request the “Road Book + Certificate” kit at a cost of €22, including postage.

The Eroica Montalcino Permanent Route

Before setting off from Montalcino, cyclists can stop for a moment at the Imperial Gardens to enjoy 360-degree panoramic views; to the north the Crete Senesi, the Montalcino hill, covered by vast expanses of vineyards and the city of Siena. To the south the beautiful countryside of the Val d’Orcia, east, the unforgettable Crete Senesi as far as the Appenines and Valdichiana and, finally to the west, the Mediterranean brush that reaches to the Tyrrhenian coast.

Terra Eroica – foto Davide Mazzocco

Halfway between the small medieval village of San Quirico d’Orcia and the splendid thermal centre of Bagno Vignoni, is Vignoni Alto that overlooks the spectacular Val d’Orcia, a UNESCO World Heritage Site. Hills, ravines, cypresses, ancient grain cultivations, many of which are organic, are the treasures of the most beautiful valley in Tuscany. Among the hills, you will find villages and monuments that overlook oak forests, olive groves and vineyards growing Brunello and other great Tuscan wines.

At the entrance to the Renaissance town of Pienza, enjoy breathtaking views of a thousand shades of yellow, red and ochre offered by the soft hills of the Val d’Orcia with Monte Amiata, the highest extinct volcano in Italy, in the background. You will also see the mighty fort of Radicofani, built on top of an 869 m high imposing basalt rock that dominates the whole area from Monte Cetona, to the Val d’Orcia to Monte Amiata.

At this point, cyclists will find themselves in the heart of the Crete Senesi, between Trequanda and San Giovanni d’Asso, an area that is characterized by continuous hills and ravines. The first are recognizable thanks to their white domed shape, while the latter for their knife-edge splits in the landscape.

Terra Eroica – foto Davide Mazzocco

Before entering Montisi, a medieval village of Etruscan origin, cyclists will come across the amazing terraces of olive groves, whose fruit gives life to the delicious Tuscan oil, which is extracted by cold-pressing the olives. Continuing on to the village of Buonconvento, vast cultivations of truffles can be seen. The white hills and ravines are the heart of this excellent Tuscan product.

Leaving Buonconvento behind and heading towards Camigliano, those lucky enough to catch a glimpse, will be able to admire the local wild fauna. Along the route, between Camigliano and Sant’Angelo in Colle cyclists will reach the Poggio alle Mura Castle, erected on a hill next to the confluence of the Orcia and Ombrone rivers. An avenue of cypresses accompany visitors to the door of the structure that is situated in the heart of the vast Brunello vineyards. Riding in the direction of Sant’Angelo Scalo, cyclists will be submerged in a world of secular olive groves before arriving at the magnificent monastery of Sant’Antimo, which is surrounded by tall cypress trees and olive groves. Then it’s back to Montalcino.

Terra Eroica – foto Davide Mazzocco
The three Eroica events in Tuscany that are the dream of thousands of cyclists all over the world 

EROICA MONTALCINO (Sunday 29 May) – Tackle one of five routes south of Siena between Val d’Arbia, the Crete Senesi and Val D’Orcia, on 29 May, strictly on vintage bicycles. Cycle among the hills of San Quirico d’Orcia, Pienza and Bagno Vignoni that have been UNESCO heritage sites since 2004.

NOVA EROICA BUONCONVENTO (Saturday 25 June) – Castelli di Buonconvento (27 km) and Valle dell’Ombrone (15 km) are the two routes with a minimum altitude designed for families and children who want to experience the thrill of the white roads. A total of five choices are available to all types of bicycles, especially gravel bikes, at the event scheduled for 25 and 26 June.

L’EROICA (1 and 2 October) – this is the king of Eroicas, the one with the L’ that distinguishes it from all the others. The one that started in 1997 with 92 participants and today counts almost 9,000 riders. Save the date: 1 and 2 October, start and finish of the five routes in Gaiole in Chianti, making history at its 25th edition.
To register: www.eroica.cc

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