Hiking among the Hermitages of the Sienese Countryside

hiking sienese countryside
  • San Leonardo al Lago Hermitage

  • Scrub Wood

  • Karst cavities

  • Lecceto Hermitage

  • Fourteenth century frescoes 

  • Lecceto Hermitage cloister

Trekking duration: 5 hours
Difficulty: low
Suitable to children: yes
Disabled accessibility: only to the Lecceto Hermitage 
Difference in level: 80 metres


Further information at the bottom of the page

Hiking among the hermitages of the Sienese Countryside

The trek between the hermitages of San Leonardo and Lecceto is a spiritual journey that links two important places of Sienese spirituality and art; immersing yourself in the greenry of the Montagnola, you will cross spaces full of history and characterized by a peaceful nature that seems to absorb, perhaps thanks to its many karst cavities, the frenzy of everyday life that continues to flow a few kilometres from this real oasis of peace.

Our starting point for the trek is the San Leonardo al Lago Hermitage, a place that by the name suggests an ancient characteristic of this area and which today, due to a decisive historical event, is something that no longer exists. A caretaker opens up access to this ancient retreat place. Crossing the corridor that once surrounded the cloister of the Augustinian hermits, we reach the door of what once was the Chapter Hall.

The restorations recently carried out in this environment have brought to light a precious masterpiece: a large Crucifixion scene. We will see together this work frescoed by Giovanni di Paolo, one of the most talented and least known artists of Sienese history, which is of a truly extraordinary expressive and technical richness: from the monochrome colouring to the exasperated gestures of the onlookers under the cross of Christ, up to illusionistic games, make this painting something unmissable.


hiking sienese countryside
Hiking sienese countryside

A moment of the hiking among the Hermitages of the Sienese Countryside

After having admired the Crucifixion, we will move inside the church, a space that, although with a single nave, will surprise you with its Gothic elegance that is completely hidden by the austere appearance of the exterior which instead presents itself with a hut shape, according to the model already adopted by the mendicant orders.

Arriving in front of the altar, I will tell you the story behind the four scenes represented on the sides of the main chapel. In the latter you will then admire, in what is the typical elegance of the Sienese fourteenth century, the Marian scenes painted by Lippo Vanni which are the Marriage of the Virgin, the Presentation of Mary to the Temple and the Annunciation. We focus in particular on this last scene, whose effects of spatial illusionism are so well studied that you will hardly understand where real space ends and where that of the painting begins.

Once we leave San Leonardo, we take the real path leading us to the Lecceto Hermitage. After a short descent, we will be faced with what is actually the only most challenging part of the entire route: with seventy-five metres in altitude over a distance of one kilometre and a hundred, we go up a very open mule track. At the end of the climb, the most covered area will begin; if we are in a summer time, it will offer a good shelter from the sun’s rays; here vegetation is typical of the Mediterranean scrub: being no more than three hundred metres above sea level and also being a relatively protected area from the currents of air, we will cross a forest mainly consisting of oaks such as holm oaks and many ericaceous.

During our trek between the hermitages we also discover where the characteristic reddish color of the soil comes from, as well as the fascinating history of the rocky component that you will glimpse beyond the soil: the cavernous limestone.

Here then you will discover how the area we will travel, apparently uniform and compact in its stratigraphic constitution, is actually punctuated by a series of cavities each with a particular name, often also due to the ancient presence of the Augustinian hermits who frequented them … After a few small differences in height, we will reach an area with a much more regular terrain, with a dirt road, therefore easy to walk. After two kilometres we will have reached the San Salvatore a Lecceto Hermitage.

hiking sienese countryside

The route between San Leonardo and Lecceto

Hiking Sienese countryside

Visiting the Lecceto Hermitage

The Augustinian nuns guardians of the hermitage

To welcome you to this place, completely surrounded by greenery, will be the pleasant view of the avenue preceding the stone entrance portal; at the end of the oaks line you will see the seventeenth-century bell tower, surrounded by a curtain wall which, if on one hand it suggests the idea of an enclosed space, on the other it will take you back to a protected and intimate dimension, just like the one cultivated by the Augustinian community of cloistered nuns who, still today – one of the few cases of continuity over the centuries of the same monastic order in the same place – guard this hermitage.

Once crossed the entrance portal, on the right you see the hermitage church that is anticipated by a portico: you will be fascinated when you realize that, under the faded-colored portico, you can still see some frescoes featuring moralizing scenes: from the figures of pious men to those of devils with bizarre wings, passing through the representation of toothed wheels crushing those who fall on them. The lively iconography of these images, which clearly clashes with the tranquility the place emanates, is linked to the ancient past of the hermitage and to the characters who lived here. We will enter the church, where almost half of the space is still reserved for the prayer of the Augustinian sisters.

The baroque appearance of the interior conceals older decorations dating back to the Middle Ages, as can be seen on some points where there are still frescoes representing saints linked to eminent Sienese characters and beyond. Among these there was also Saint Catherine of Siena, who came to Lecceto several times to meet an important Augustinian friar from Oxford …

We will conclude the visit of the Hermitage with the large cloister, an elegant Renaissance space in which the frequent appearance of the Piccolomini coat of arms reveals, as we will see, the attention that the illustrious Sienese family paid to this complex, to such an extent to dedicate some important artistic commissions to it.

We conclude our trek through the Hermitages returning to San Leonardo al Lago and we will do it by following a small variant that after a while take us back to the route taken on the outward journey, this time admiring glimpses that we had previously missed. If once you have finished the journey you will feel your legs a little tired, your spirit will have fully recovered, because you will have unexpectedly found in nature two important pieces of art and spirituality in the land of Siena.

san leonardo al lago

Visiting San Leonardo al Lago Hermitage

Lecceto Hermitage

The Lecceto Hermitage

This trekking can also be booked in combination with the other available tours on Siena and Florence, which can be consulted in the Menu. This activity was born in collaboration with the colleague Ambra Tour Guide.

Trekking shoes and a layered outfit are recommended for the route.
This activity can be booked and customized, depending on the schedule and the customer’s needs.

The nature guide or guides who carry out this activity are covered by liability insurance. The meeting point to start of the activity coincides with the final point as it is a ring route trekking.
There will be a mid-way lunch / snack break, with packed lunch.

The nature guide is not a tourist agency, so he/she does not provide tastings service, lunches or dinners and only provides the clients the contacts for external services.

To get further information, to book the tour or to get the contact of a licensed driver providing private transfer service, please write to: