The small museum of Castiglione d'Orcia is located in the former oratory of San Giovanni Battista, dating back to the end of the 16th-beginning of the 17th century, and houses three real masterpieces that make this exhibition space a destination not to be missed for those who goes to Val d'Orcia. In the museum there are, in fact, the paintings made for Castiglione and Rocca d'Orcia by some of the major exponents of the Sienese school of the fourteenth and fifteenth centuries: Simone Martini, Lorenzo di Pietro known as il Vecchietta and Giovanni di Paolo, with three splendid Madonnas with Baby. These are then joined by a series of liturgical furnishings from churches and brotherhoods in the area, including two molds for blessed bread and hosts.

Leaving the museum, you reach the top of the village from which you can see the imposing Rocca di Tentennano, to which you can climb through a suggestive walk of 300 meters. The landscape along the road opens onto the rolling hills of the Val d'Orcia and Montalcino. The tower, which stands 20 meters high on a limestone spur, is remembered for the first time in 853 as a possession of the abbey of Monte Amiata and always had a strategic role of great importance due to its privileged position on the Via Francigena .

The fortress belonged to the Sienese Salimbeni family in the fourteenth and fifteenth centuries and, in 1367, Saint Catherine of Siena stayed there, who, as an illiterate, received the divine gift of writing right here. Today the fortress is open to the public and hosts art exhibitions. Going up on the terrace, the view that presents itself to the visitor certainly repays the effort: the view ranges from Monte Amiata to the south, to Monte Cetona to the south-east up to the first offshoots of the Apennines to the east and north.