Castiglione d'Orcia

One of the most fortified towers in central Italy, perched just above the Via Francigena and Via Cassia.


Castiglione d’Orcia is a small hamlet in the centre of Val d’Orcia, on one of the slopes of Monte Amiata. The first records of the town’s existence date back to 714, when the small settlement belonged to the Aldobrandeschi family and was known as Petra.

In 1274, when all the possessions of the Aldobrandeschi family were divided, Castiglione d’Orcia became part of the county of Santa Fiora, and soon after became under the possession of Siena. The Republic gave the town in concession to two families, the Piccolomini and then the Salimbeni in return for financial favours. The two families used Castiglione d’Orcia as the base from which they planned the revolution against the Republic of Siena.

A frazione of Castiglione d’Orcia is the hamlet of Vivo d’Orcia, from which two rivers: the Vivo and Ermicciolo are born - two of the river Orcia’s main affluents. The river Ermicciolo is also extremely important as it supplies the aqueducts of Siena and Val di Chiana


La Rocca di Tentennano

The reason behind the fort’s construction is pretty intuitive. Perched high upon a steep hill, practically unreachable if not by one road which would be constantly under surveillance. A hill from which one could meticulously check upon the Via Francigena which runs just below the hill. On the other side one can see - and check - the roads that lead to the Maremma and Tuscan coast. An untouchable fortress who’s origins date back to 853. Throughout the years it passed into the hands of many different owners, from the Salimbeni who claimed ownership for the whole of the 14th century. The Republic of Siena only managed to get back control over it thanks to a traitor within the Salimbeni’s crew who opened the front doors for them. Many years later, when the Republic of Siena was dismantled and the Rocca, as well as all of Castiglione d’Orcia, fell under Florence’s jurisdiction, it only occurred because one again, a traitor opened the doors for them.

An array of famous people sojourned in the Rocca throughout the ages, perhaps the most notable figure being Santa Caterina da Siena, in the year 1377. Legend has it that the saint learned how to read and write whilst in the Rocca—by miracle.

The hamlet below and surrounding the Rocca used to act as the first layer of defense, and the fortresses walls have a thickness of 3 meters (9.8 feet).

Image by @saretta_gu

L’eremo del Vivo

Image by @saretta_gu

Situated on the outskirts of Castiglione d’Orcia, the Eremo del Vivo is a spiritual construction who’s date and reason of construction, in the middle of the woods, remains uncertain. An Eremo is a place where one would go when they wished to dedicate themselves to a life of prayer and contemplation, a remote place where one could seek solitude. It was most likely built in the 11th century and is attributed to Saint Romolo. The first mentions of the Eremo del Vivo date back th 1113, when it was cited as one of the structures belonging to the Monastery of Camaldoli. The initial structure was of the Eremo and a convent, used by Pope Alessandro IV to hide monks during periods of civil unrest. The ruins of the convent were later built upon on behalf of the Cardinal of Montepulciano who requested a castle to be built in the 13th century. L’Eremo sits in the middle of wooded areas with rich water sources.

Bagni San Filippo

Beautiful natural formations with hot spring waterfalls in the middle of a forest, Bagni San Filippo are an obligatory stop when in Val d’Orcia. An easily accessible path leads you from the parking lot into the woods, where you’ll immediately spot bright blue hot water pools in front of a huge white rock formation (calcium) which is known as the Balena Bianca (the white whale). For safety reasons it is no longer allowed to climb the waterfall, but there are many pools from which you can enjoy the wonderful view.

Image by Eventi e Sagre


Image by Eventi e Sagre

July - Sagra della Polenta, Vivo d’Orcia
August - Sagra del Crostino, Castiglione d’Orcia
October - Sagra del Fungo e della Castagna, Vivo d’Orcia

Image by Perillà


Osteria Perillà

contemporary fine dining

Delicious and researched food just below the Rocca di Tentennano, spoil yourself with a fantastic meal in this one Michelin Star osteria.

Image by @mattiafortu

La Cisterna nel Borgo

rustic & traditional

Traditional Tuscan comfort foods in a welcoming family atmosphere, from ribollita soups to maltagliati with fennel and ragù.