Situated on a hilltop, nestled in the Val d’Orcia, in a splendid panoramic position, Castiglione d’Orcia is, as its name indicates, an ancient castle that saw its development thanks to its strategic location on the Via Francigena. For centuries the stronghold of the Aldobrandeschi family, the Rocca Aldobrandesca rises above the village, where the imposing keep, walls and other rooms can be visited.

The ancient town hall overlooks the charming Piazza Vecchietta, which owes its name to the painter Lorenzo di Pietro known as il Vecchietta for a long time believed to be a native of here. A few steps from the square is the Church of Saints Stephen and Degna, which houses a valuable panel painting by Sienese painter Pietro Lorenzetti.

A municipality since 1252, at different times it has annexed the surrounding villages to its territory until it took on its present characteristics in 1867, which is why it boasts a wealth and variety of environments and locations: Campiglia d’Orcia, Gallina, Vivo d’Orcia and the Bagni San Filippo spa area while, just opposite Castiglione, in the shadow of the Tentennano Tower, is located the small medieval village of Rocca d’Orcia.