16 Best Sights in Tuscany, Italy

This 1,000-year-old village is worth a stop—skip the nondescript new town and head straight to the centro storico to explore winding stone streets with tiny churches around every corner. The abbey for which the town was named was founded in 743; its current appearance reflects an 11th-century renovation, but the original crypt remains intact. The tourist office in town has hiking-trail maps for Monte Amiata.

Some 10 km (6 miles) south of La Verna on SR54 is the small hilltop town where Michelangelo Buonarroti, sculptor, painter, architect, and poet, was born on March 6, 1475. During two weekends in mid-October, Caprese Michelangelo's very lively Sagra della Castagna (Chestnut Festival) takes place. Among the many delights that feature in the fair, the freshly made castagnaccia (a typically Tuscan dessert made with chestnut flour, pine nuts, olive oil, and rosemary) is a must-try.

Follow SP19 past Sarteano and continue on SP21 to reach this delightful village. Time may seem to have stopped as you walk along the quiet, narrow, medieval lanes and back alleys. Peer through the locked gate for a glimpse of the privately owned castle, and take in splendid views of olive orchards, cypress groves, and the quiet wooded slopes of Mt. Cetona from the town's terraced streets.

This walled medieval town, 3 km (2 miles) northeast of Chianciano Terme, is best known for its proximity to the nearby spas. Nevertheless, the well-preserved center has an appeal all of its own.

The largest town in southern Tuscany, Grosseto is the capital of the Maremma. First recorded in the 9th century as a castellum (small fort) built to defend a bridge and a port on the nearby River Ombrone, the town is now a thriving agricultural center. Badly damaged during World War II, it has been largely rebuilt since the 1950s, but a small centro storico, protected by defensive walls that follow a hexagonal plan, is worth a short visit on your way to the coast.

On the south side of Elba, this small town with a long sandy beach and protected cove is a classic summer vacationer's spot. The laid-back marina is full of bars, boutiques, and restaurants.

A tiny hilltop hamlet, about 2 km (1 mile) west of Greve in Chianti, Montefioralle is the ancestral home of Amerigo Vespucci (1454–1512), the mapmaker, navigator, and explorer who named America. (His cousin-in-law, Simonetta, may have been the inspiration for Sandro Botticelli's Birth of Venus, painted sometime in the 1480s.)

This sleepy town, sitting on a small knoll about 15 km (9 miles) south of Sansepolcro, would probably attract little attention if not for the fact that, in the 1450s, Piero della Francesca painted one of his greatest masterpieces—the Madonna del Parto, a rare image of a pregnant Virgin Mary—here.

If you're heading northwest to Siena, stray 9 km (5½ miles) west of the Via Cassia to Vescovado and then follow the signs 2 km (1 mile) south to this tiny fortified medieval borgo (village) that has been completely restored.

The waters of the port at Elba's eastern end are noticeably azzurro (sky-blue). It's worth a stop for a walk and gelato along the rows of yachts harbored here.

On the southeastern side of Monte Argentario, this small port town is the haunt of the rich and famous, with top-notch hotels and restaurants perched on the cliffs.

On the north side, busy and colorful Porto Santo Stefano is Monte Argentario's main center, with markets, hotels, restaurants, and ferry service to Giglio and Giannutri, two of the Tuscan islands.

The lively port town where Victor Hugo (1802–85) spent his boyhood makes a good base for visiting Elba. Head right when you get off the ferry to get to the centro storico, fortified in the 16th century by the Medici grand duke Cosimo I (1519–74). Most of the pretty, multicolor buildings that line the old harbor date from the 18th and 19th centuries when the boats in the port were full of mineral exports rather than tourists.

Elba's quietest town is an old-fashioned port on the northeastern edge of the island. Here you'll find a pebble beach, an old mine, a leafy public park, and ferry service to Piombino.

To the southeast of Chianciano, 10 km (6 miles) along SP19, lies this relatively unspoiled village that dates from the 12th and 13th centuries. The town's narrow streets, which wind slowly up toward an imposing fortress, now privately owned, make for very pleasant strolling.

A steep gravel road leads north out of Bagno Vignoni for 2 km (1 mile) to the town's upper village, a tiny grouping of buildings huddled at the base of a 13th-century tower. The tower, now a private home, was built to watch over the Via Francigena. A spectacular view of the entire Val d'Orcia opens up from the eastern gate.