Castiglione d’Orcia, situated on the ridge of a hill near the Cassia road, is easily recognizable for its imposing tower, Rocca degli Aldobrandeschi, which maintains untouched the medieval atmosphere. Among the many suggestive spots to discover is the is the principal square named after the painter il Vecchietta with its jutting out town hall and the characteristic cobblestone pavement geometrically shaped in brick edged squares and the XVII century travertine well in the middle.
Among the most important buildings is the Pieve dei Santi Stefano e Degna with the worshipped painting of the Madonna delle Grazie by Pietro Lorenzetti. The small church of the XIII century of Santa Maria Maddalena and its exhibition of works of art, altar clothes and holy vessels is worth a visit. Among its masterpieces are paintings by Simone Martini, Giovanni di Paolo and Vecchietta.