Castiglion Fiorentino is a small, walled city located near Arezzo and Cortona. The earliest mention of Castiglione dates to the 10th century, when it was an estate owned by the Marquise of Monte Santa Maria. It was once strategically important, highlighted by several architectural structures, like the imposing town walls and the impressive fortified Cassero. Because of this importance, over the centuries, it passed from ruler to ruler before it became part of the Grand Duchy of Tuscany, dominated by the Medici family. The history of Castiglion Fiorentino stretches back even further, however, as seen by recent archeological discoveries which brought to light its status as a vital centre of Etruscan civilization in the Valdichiana.
Some main sites in the town worth seeing are the Church of Sant’Angelo al Cassero, where, during restoration, a stretch of the Etruscan town wall dating to the 4th century BCE was discovered in the crypt, as well as Piazzale del Cassero, where an excavation has unearthed a sanctuary, the castle walls, an Etruscan gate also dating to the 4th century BCE, the Casseretto, Palazzo Pretorio and the Archeological Museum.