Castiglion Fiorentino – en route between Cortona and Arezzo

Set on the last hill overlooking the Val di Chiana plain between Cortona and Arezzo, Castiglion Fiorentino is an untouristy Tuscan borgo. Seen from afar, this fortified village looms large in the distance. It was a stronghold belonging to Arezzo until the Florentines snatched it in 1384. Today, Castiglion Fiorentino still feels very medieval, bounded by thick walls and crowned by the Cassero, a hulking medieval fortress. Even so, Renaissance touches abound. On the old market square are Vasari’s famous loggias, with stone arches framing a fine vista of the rooftops and surrounding countryside. This well-preserved medieval settlement has an unusually high number of churches. The oldest of these, the Pieve Vecchia, displays a Signorelli fresco of the Deposition of Christ (1451), while the Romanesque-Gothic church of San Francesco contains a sculpted version. Other sacred works and gold and silverware from the surrounding churches can be seen in the quirky collection in the Pinacoteca, on via del Cassero. Just outside the village is the octagonal temple of Santa Maria della Consolazione.

Looming beyond the village, and visible from the Cassero fortress, are the dilapidated battlements of the Castello di Montecchio Vesponi. This crenellated medieval castle once belonged to the legendary English condottiero John Hawkwood, a 14th-century captain and commander. After serving the Florentines well, the former mercenary became an honorary Florentine citizen.

Address: Torre del Cassero, via del Tribunale, Castiglion Fiorentino
Web: www.museicastiglionfiorentino.it