Strade di Siena > Horseback riding around Siena |

Siena, horse trekking with a medieval flavor

A ring all around the City of the Palio, and others path without particular technical difficulties for a scenic horse trekking that in three, four or five days leads on a tour through some of the most characteristic territories of the Sienese area.

From the visit to the marvelous Castle of Monteriggioni, a unique medieval structure still preserved intact despite the centuries and battles, to the vineyards that branch out on the sides of the sinuous Chianti hills and that start right from the borders of the City of Siena, the horseback trail provides an overview of the outer areas of the city that overlook the Montagnola Senese, Chianti and the Crete Senesi.

The stables and stops along the way are ready to welcome visitors and their horses, but above all they make it possible to experience the typical food and wine products of the place, such as a nice plate of Pici or a good Chianti wine.

All this becomes even more fascinating if the companion of this experience is the horse, protagonist and undisputed symbol of the territory, which will be able to give moments of closeness to nature and absolute freedom, which will make the experience even more unforgettable.

Crossed Areas


One of the most incredible and characteristic cities of art, with intact medieval beauty and unquestionable charm. Siena is identified above all with the unmistakable Piazza del Campo, the Piazza del Palio, which suddenly reveals itself in the alleys of the center, dominated by the imposing Torre del Mangia. Siena is art, tradition and food and wine, it is a slow stroll among the buildings and palaces that characterize each “Contrada”. It is an experience to be done slowly and to be discovered step by step.



Immersed in the typical Sienese countryside, Mociano – just outside the city of Siena – is a well-known place because horses are trained and run here for the Palio di Siena.

Montagnola Senese

Strongly naturalistic area that laps the city of Siena and extends into the municipalities of Casole d’Elsa, Monteriggioni and Sovicille. Woods and Mediterranean scrub are home to unique animal species and alternate with rivers, aquifers, karst caves and deposits of “torre stone” (the Sienese yellow marble). Place of origin of the Cinta Senese and crossed by the Via Francigena, the Montagnola Senese accompanies the visitor among its numerous castles, parish churches and hermitages.


It is no coincidence that in Dante’s Divine Comedy there was a “round circle” that “crowns itself with towers”: Monteriggioni is a typical intact medieval castle, where time seems to have stopped. Suggestive from the outside, delightful inside, with shops and shops, small houses, surrounded by thick walls and 15 fortified towers. A blast from the past a stone’s throw from Siena.

Val d’Arbia

Intersected largely with the Crete Senesi territory, the Val d’Arbia is a limited area that extends from the gates of Siena, along the Via Francigena, following the Arbia river. Many inhabited centers along the route alternate with small hidden gems, such as the characteristic village of Lucignano d’Arbia.

More di Cuna

More di Cuna is the most “modern” part of the ancient Cuna locality. As in the nearby Monteroni d’Arbia, this was also an area that was characterized by the hospitality given to the pilgrims of the Via Francigena.


It is on these hills that one of the most famous DOCG red wines in the world is born. The Chianti area extends between Siena, Florence and Arezzo and absorbs the peculiarities of each area, although the whole area is characterized by vineyards and hills dotted with small typical villages, mostly born from ancient fortified border settlements.


A small town on the outskirts of Chianti, Quercegrossa is literally divided between the municipalities of Castelnuovo Berardenga and Monteriggioni. Just outside the center, in the area of the ancient mill, there is one of the largest swimming pools in Tuscany.