The village starts from Porta Fiorentina, the centuries-old entrance in the north of the village that leads to the historical centre. Just beyond the square is the Church of San Francesco, a fascinating Romanesque building with the occasional Gothic element, dating back to the second half of the 13th century.
Take a visit to the Piazza del Municipio, where you’ll find the Municipal Picture Gallery housed in the Church of Sant'Angelo; treasured 13th century goldsmith's works and some valuable paintings by Margarito, Taddeo Gaddi, Bartolomeo della Gatta and Giorgio Vasari are also kept here.
Vasari's 16th century loggia, dating back to 1513, is just opposite the Palazzo Comunale. From this architecturally astounding spot you can take in the stunning view of the Val di Chio along with Valdichiana and Valtiberina.
The Civic Archaeological and Underground Archaeological Excavation Museum is another important monument located inside Palazzo Pretorio. The museum collects archaeological relics found in the Castillian and Cassero areas. The partial reconstruction of an Etruscan sanctuary’s roof is particularly interesting and dates back to between the end of the 5th and the beginning of the 4th century BC.
The Museum of Sacred Art of the Pieve (or Collegiata dei Santi Michele e Giuliano) is also well worth a visit, housing works from the 15th and 17th centuries, including the fresco Mourning over the Dead Christ by Luca Signorelli and an altarpiece by the Della Robbia workshop depicting the Baptism of Christ.
Among the multitude of other attractions in Castiglion Fiorentino, we recommend taking a trip to the Municipal Theatre, a beautiful structure with three tiers of platforms. The inside is decorated in a beautiful nineteenth-century style, with refined golden stuccoes and elegant marbled plaster.