Driving Tours

En Route to Cortona

From Sansepolcro, it's a 15km (9-mile) jaunt across the border to Umbria. If you haven't finished with Tuscany, you can head back toward Arezzo, turning south on the SS71 to go down the wide Chiana Valley (Valdichiana), famous for its snowy-white cattle that make such excellent bistecca fiorentina, toward Cortona.

Along the way, you'll pass Castiglion Fiorentino, a fortified medieval town dominated by a pronglike tower, the Torre del Cassero. The tourist info office is at Piazza Risorgimento 19 (tel. 0575-658-278; fax 0575-659-457). It's open Tuesday through Sunday from 9:30am to 12:30pm and 3:30 to 6:30pm, but may keep shorter hours in winter. The center of town is Piazza del Municipio, bordered by a 16th-century loggia supposedly by Giorgio Vasari. Just above this is the deconsecrated church of Sant'Angelo, now the entrance to the Pinacoteca Comunale, Piazza del Municipio 12 (tel. 0575-657-466). Its well-labeled collections include some medieval gilded copper crosses, a Taddeo Gaddi Madonna and Child, and an odd Bartolomeo della Gatta St. Francis Receiving the Stigmata. (Tradition holds the other friars nearby weren't awake when Francis was visited by the seraph, but here one clearly is.) There's a good view from a tower here. The museum is open Tuesday through Friday from 10am to 12:30pm and 4 to 6:30pm (until 7pm Sat-Sun). Admission is 3€ adults and 2€ children, or 5€ if you want to tack on a visit to any of the town's other museums. Next door to the Palazzo Pretorio is a tiny museum of Etruscan remains found in the area. Also worth calling on is the Collegiata, 300m (984 ft.) away on Piazza San Giuliano, with a Madonna Enthroned with Saints by Bartolomeo della Gatta on the third altar on the right, Lorenzo di Credi's Adoration of the Child in a chapel to the right of the high altar, and a huge Maestà by Segna di Bonaventura in the left transept. The Pieve next door (ask the Collegiata sacristan to unlock it) preserves a Deposition by Signorelli's school. On the edge of town is the High Renaissance templelike church of Madonna della Consolazione, an octagonal structure built in the 16th century.

A bit farther south along the SS71, you'll see the 13th-century walls of Montecchio Vesponi off to the left. The Florentines gave this castle to the English condottiere John Hawkwood (the gentleman in Paolo Uccello's equestrian painting in Florence's Duomo), who had fought battles for them.