Val d'Orcia
Val d'Orcia

Guide to visit Castiglione d’Orcia

Castiglione, a hamlet in the heart of the Val d’Orcia

Castiglione d’Orcia rises at an altitude of 540 meters above a hill that rises on the valley floor of the River Orcia. Typical rustic Tuscan village, it has its center in the square dedicated to the painter Lorenzo di Pietro called il Vecchietta.

The first news of the village dates back to 714 when it appeared among the possessions of the powerful Aldobrandeschi family. In 1252, Castiglione became a free municipality, but already during the fourteenth century it entered the orbit of the Republic of Siena which granted control of the hamlet to the Piccolomini family first and to the Salimbeni then. When Siena was definitively defeated by Florence, Castiglione also became part of the Florentine territories.

Piazza Vecchietta in Castiglione d'Orcia
Piazza Vecchietta in Castiglione d’Orcia (Photo by Fabio Poggi / CC BY)

What to see in Castiglione d’Orcia

Castiglione d’Orcia is truly a delightful village capable of giving many surprises. The main points of interest are Piazza Vecchietta where there is a beautiful travertine well from the 16th century, the Rocca Aldobrandesca, the Pieve dei Santi Stefano e Degna, the Chiesa di Santa Maria Maddalena and the Sala d’Arte San Giovanni which is located in the seat of the Confraternity of San Giovanni.

Rocca Aldobrandesca

The most important monument of the village is the Rocca Aldobrandesca, of which large sections of walls and most of the donjon remain. The fortress was owned by the Aldobrandeschi first and then Siena and, as well as the nearby Rocca a Tentennano, it was placed in the domain of the very important via Francigena.

Rocca Aldobrandesca in Castiglione d'Orcia
Rocca Aldobrandesca in Castiglione d’Orcia (Photo by Senpai / CC BY )

Pieve dei santi Stefano e Degna

Nearby, in peripheral location is the pieve dei santi Stefano e Degna (parish church of the Saints Stephen and Degna). Of medieval Foundation, the Church has a beauty 15th-century portal.
Inside are preserved frescoes of the Sienese School of the early 16th century and a big painting “Madonna in trono col Bambino e santi” (Madonna enthroned with Child and saints), dated 1531, by Giovanni di Bartolo. Other works from this church and attributed to Simone Martini, Pietro Lorenzetti and Vecchietta, were transferred in the Pinacoteca (art gallery) of Siena.

Castiglione and Rocca d'Orcia Pieve dei Santi Stefano e Degna
Pieve dei Santi Stefano e Degna a Castiglione d’Orcia (Photo by LigaDue / CC BY)

Sala d’Arte San Giovanni

Located in the heart of the village, inside the headquarters of the Confraternity of San Giovanni, the Sala d’Arte San Giovanni houses some works of great value created by some great masters of the Sienese school of the XIV and XV centuries: Simone Martini, Giovanni di Paolo and Lorenzo di Pietro known as Il Vecchietta. In addition to the works of these masters, some liturgical furnishings from the churches of Castiglione and the surroundings are also kept here.

For information on opening hours and tickets, I recommend you visit the Musei Senesi website.

What to see near Castiglione d’Orcia

Castiglione d’Orcia is located in an absolutely central position in the Val d’Orcia. Its municipal area is full of points of interest that can be reached very quickly. The main ones are:

Rocca d’Orcia

Rocca d’Orcia is really a stone’s throw from Castiglione d’Orcia (in the sense that you can literally walk there!). This tiny village is characterized by the presence of a beautiful fortress, the Rocca a Tentennano, which pairs with the Rocca Aldobrandesca in Castiglione. The fortress rises imposingly on a spur of rock and offers a breathtaking panoramic view that sweeps from Monte Amiata to the Terre di Siena.

Bagni San Filippo

Bagni San Filippo is one of the most fascinating spas in all of Tuscany. In this small center we find both an equipped spa and free spas. In particular, the free spas are located in a truly unique and suggestive context.

Ripa d’Orcia

Located in a beautiful position a few kilometers from Castiglione, Ripa d’Orcia is a small medieval village historically linked to the Republic of Siena. The main points of interest are the Church of Santa Maria della Neve and above all the Castle of Ripa d’Orcia which today is used as a hotel.

Ripa d'Orcia
Ripa d’Orcia (Photo by Eugen Kalloch / CC BY)

If you are organizing an itinerary in Val d’Orcia, I recommend that you consider both the other main centers Montalcino, San Quirico d’Orcia, Pienza and Radicofani, that the thermal center of Bagno Vignoni and the wonderful Abbey of Sant’Antimo.

How to get to Castiglione d’Orcia

Castiglione d’Orcia is located about 55 kilometers away from Siena, about an hour’s drive.

By car: from Siena take the Strada Regionale 2 Cassia to Bagno Vignoni; from there continue on SP323 to your destination.
Those coming from the south on the A1 motorway must take the Chiusi / Chianciano exit and then continue on the SP146 towards Chianciano Terme. From there you must follow the signs for Castiglione d’Orcia which is about 25 kilometers away.

By bus: from Siena you must take the 112 line to San Quirico d’Orcia and then the 52A line to Castiglione; both connections are managed by Siena Mobilità.

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