Castiglione d'Orcia is a medieval hill village about 8 kilometres south of San Quirico, less visited than its neighbours but arguably more atmospheric. The village is perched on a ridge above the Orcia valley with views in every direction. At its heart is the tiny Piazza il Vecchietta, named for the 15th-century Sienese painter Lorenzo di Pietro (known as il Vecchietta), who was born here — there is a fresco of his in the small church of Santi Stefano e Degna.
The ruined Rocca Aldobrandesca castle above the village dates from the 12th century and offers the best panoramic view of the Val d'Orcia from any point near San Quirico. The walk up takes about twenty minutes from the car park, and on a clear day you can see all the way to Monte Amiata and the distinctive profile of Pienza on the ridge to the west.