The small museum of Castiglione d’Orcia is located in the former Oratorio di San Giovanni Battista (Oratory of St. John the Baptist), which dates back to the late 16th-early 17th century. Contained within are genuine masterpieces that make the exhibition space a must-see for visitors travelling through the Val d’Orcia.
The museum houses paintings created for Castiglione and Rocca d’Orcia by leading exponents of the Sienese School from the 14th and 15th centuries: Simone Martini, Lorenzo di Pietro (also called “Il Vecchietta”) and Giovanni di Paolo, in three extraordinary Madonnas with Child.
Along with these works, there is a collection of liturgical furnishings from churches and confraternities of the surrounding area, including two moulds for consecrated bread and sacramental hosts.
Leaving the museum, visitors may continue on to the summit of the town, and from there view the Rocca di Tentennano. This fortified tower is reached by walking along a breathtaking 300-metre pathway. The view of the countryside looks out to the gentle hills of the Val d’Orcia and to Montalcino. The tower itself, rising some 20 metres from a limestone spur, was first documented in 853 as a possession of the Abbey of Monte Amiata. For centuries it served a role of great strategic importance as a vantage point over the Via Francigena.
In the 1300s and 1400s, the fortress belonged to the Salimbeni family from Siena. In 1367, Saint Catherine of Siena visited here and, though illiterate, received the divine gift of writing.
Today the rocca is a site for art exhibitions. It is open to the public, and visitors who climb up to the terrace are rewarded by a magnificent panorama: the view takes in Monte Amiata to the south, Mount Cetona to the southeast, and reaches all the way to the Appenine Mountains to the east and the north.
Madonna col Bambino (Madonna with Child), Simone Martini (1320-1325), Sala d’arte San Giovanni (St. John Room of Art): an exceptional work portraying the relationship between Mother and Son, powerfully evident in the gazes and gentle touches. The Infant clutches a small swallow in his hand as though it were a toy.
Rocca di Tentennano: the view from the top of the tower looks out over the velvety hills of the Val d’Orcia countryside, which UNESCO declared a World Heritage Site. An experience that will never be forgotten!

Sala d’Arte San Giovanni
via San Giovanni, 8
53023 Castiglione d’Orcia
Rocca di Tentennano
Loc. Rocca d’Orcia
53023 Castiglione d’Orcia
OPENING HOURS
Sala d’Arte San Giovanni
Saturday and Sunday: 4 PM – 6 PM
Rocca di Tentennano
Everyday: 10.30 AM – 1 PM | 2.30 PM – 6 PM
**
TICKETS
regular: € 3,00
reduced: € 1,50
free: children under 6 years
In the centre of an area that boasts many strongholds, towers, and fortifications, the town of Castiglione is built around an ancient fortress, along with the Rocca Aldobrandesca, and it still maintains its Medieval urban layout. During the 1300s the town belonged to Siena, which in turn granted it to powerful families in exchange for favours of a financial nature. Thus it was that, paradoxically, the Piccolomini family and later the Salimbeni family used Castiglione d’Orcia as their base during the revolt they launched against Siena itself.
At the centre of the main piazza, with its distinctive 18th-century paving in brick and cobblestones, stands a beautiful well in travertine. The piazza is named after the 15th-century Sienese painter Lorenzo di Pietro, known as “il Vecchietta”. Though the artist was not born here (as was previously believed), he always had close ties to this town.