Like the other villages in this enchanting area, Castiglione is enticing not just thanks to its beautiful landscape, but also for its numerous remarkable artistic works that are kept in its distinctive historical centre.
Piazza Vecchietta is at the centre of the village, and is dedicated to the artist Lorenzo di Pietro (1412-1480), a famous painter, sculptor and architect nicknamed ‘il Vecchietta’ who is presumed to be a native of Castiglione. The Palazzo del Comune and other medieval buildings overlook the intriguing heart of the village. Visits to the ancient church of Santa Maria Maddalena, a Romanesque stone building and the church of Santi Stefano e Degna, the most important religious building in the village, are all unmissable.
The Sala d'Arte San Giovanni, a small museum located in the former oratory of San Giovanni Battista, houses the paintings made for Castiglione and Rocca d'Orcia by some of the greatest exponents of the Sienese school in the 14th and 15th centuries: Simone Martini, Lorenzo di Pietro known as il Vecchietta and Giovanni di Paolo, with three magnificent works depicting the Madonna with Child.
The impressive Tentennano Fortress, which stands on a limestone spur, towers over Castiglione d’Orcia. Built in the 13th century by the Tignosi Counts from Tintinnano, in the 14th and 15th centuries it belonged to the Salimbeni family from Siena. The impressive fortress, where Saint Catherine of Siena also stayed, had a consistently important strategic function for controlling the southern territory of the historic Sienese state.