86 Best Sights in Tuscany, Italy

Behind the church of San Galgano, a short climb brings you to this charming little chapel with frescoes, by painter Ambrogio Lorenzetti (documented 1319–48), and a sword in a stone. Legend has it that Galgano, a medieval warrior and bon vivant, was struck by a revelation on this spot in which an angel told him to give up his fighting and frivolous ways forever. As a token of his conversion, he plunged his sword into the rock, where it remains today.

A drive through the park, especially on the very winding 34-km (21-mile) road between the Monastero di Camaldoli and Santuario della Verna, passing through the lovely abbey town of Badia Prataglia, reveals one satisfying vista after another, from walls of firs to velvety pillows of pastureland where sheep or white cattle graze. In autumn, the beeches add a mass of red-brown to the palette, and, in spring, torrents of bright golden broom pour off the hillsides with an unforgettable profusion and fragrance.

Walking the forests—which also include sycamore, lime, maple, ash, elm, oak, hornbeam, and chestnut trees and abundant brooks and impressive waterfalls—is the best way to see some of the wilder creatures, from deer and mouflon (wild sheep imported from Sardinia in 1872) to eagles and many other birds, as well as 1,000 species of flora, including many rare and endangered plants and an orchid found nowhere else. The park organizes theme walks in summer and provides English-speaking guides anytime with advance notice.

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.

Against the walls of San Quirico d'Orcia, these Italian-style gardens retain merely a shimmer of their past opulence. They were planted in 1581 by Diomede Leoni—hence the name of the park. In the center there's a 17th-century statue of Cosimo III, the penultimate Medici grand duke of Tuscany.

Il Ponte della Maddalena is, oddly, also known as the Devil's Bridge. Commissioned in all likelihood by Matilde di Canossa (1046–1115), it was restructured by the petty despot Castruccio Castracani in the early 14th century. It's worth the climb to the middle—the bridge is narrow, steep, and pedestrians-only—to check out the view. Despite 1836 flood damage and early-20th-century alterations, it seems little changed from the Middle Ages. If you're heading north along the Serchio from Lucca to Bagni di Lucca, you will see the bridge on your left.

Walk along Via San Lino, through Porta San Francesco, and out Borgo Santo Stefano into Le Balze—a haunting, undulating landscape of yellow earth drawn into crags and gullies that's thought to be the result of rainwater wearing down the soil substructure. This area was originally part of the Etruscan town of Velathri, as evidenced by walls that extend 1 km (½ mile) toward the old Porta Menseri. Toward the end of the road, on the right, is the church of San Giusto (with terra-cotta statues of the town's patron saints) built to replace an earlier church under which the earth had eroded. The bus for Borgo San Giusto, leaving from Piazza Martiri, goes through Le Balze (about 10 runs per day).

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.

The highest point on Elba, Monte Capanna is crossed by a twisting road that provides magnificent vistas at every turn; the tiny towns of Poggio and Marciana have enchanting little piazzas full of flowers and trees. You can hike to the top of the mountain or take an unusual open-basket cable car from just above Poggio.

The older town, Montecatini Alto, sits atop a hill nearby, and is reached by a funicular from Viale Diaz. Though there isn't much to do once you get up there, the medieval square is lined with restaurants and bars, the air is crisp, and the views of the Nievole, the valley below, are gorgeous.

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. It's now on display in Sansepolcro's Museo della Madonna del Parto.

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.

Pre-Etruscan tombs at this necropolis aren't kept up well, but they're interesting simply for their age, as they're even older than Saturnia's legendary baths. Access is free and at all hours.

Founded in the 13th century, this still-functioning hospital has a facade with a superb early-16th-century exterior terra-cotta frieze. It was begun by Giovanni della Robbia (1469–1529) and completed by the workshop of Santi and Benedetto Buglioni between 1526 and 1528. Don't miss the 17th-century graffiti on the columns outside.

Montepulciano's town hall dates from the late 13th century, though it was restructured in the 14th century and again in the mid-15th century. Michelozzo oversaw this last phase, using the Palazzo Vecchio in Florence as his inspiration. From the tower, a commanding view of Siena, Mt. Amiata (the highest point in Tuscany) and Lake Trasimeno (the largest lake on the Italian peninsula) can be enjoyed on a clear day.

Radda's town hall (aka Palazzo Comunale), in the middle of town, was built in the second half of the 14th century and has always served the same function. The 51 coats of arms (the largest is the Medici's) embedded in the facade represent the past governors of the town, but unless you have official business, the building is closed to the public.

Across the piazza from the Collegiata is the "old" town hall built in 1239. Its tower was erected by the municipality in 1255 to settle the raging "my-tower-is-bigger-than-your-tower" contest—as you can see, a solution that just didn't last long. The palace is closed to visitors.

The piazza, with its fine Renaissance Palazzo dei Cavalieri, Palazzo dell'Orologio, and Chiesa di Santo Stefano dei Cavalieri, was laid out by Giorgio Vasari in about 1560. The square was the seat of the Ordine dei Cavalieri di Santo Stefano (Order of the Knights of St. Stephen), a military and religious institution meant to defend the coast from possible invasion by the Turks.

Also in this square is the prestigious Scuola Normale Superiore, founded by Napoléon in 1810 on the French model. Here graduate students pursue doctorates in literature, philosophy, mathematics, and science. In front of the school is a large statue of Ferdinando I de' Medici dating from 1596. On the extreme left is the tower where the hapless Ugolino della Gherardesca (died 1289) was imprisoned with his two sons and two grandsons—legend holds that he ate them. Dante immortalized him in Canto XXXIII of his Inferno. Duck into the Church of Santo Stefano (if you're lucky enough to find it open) and check out Bronzino's splendid Nativity of Christ (1564–65).

The town's main square teems with cafés and bars. It's an excellent spot for people-watching; in the evening and on weekends it seems like everyone is out walking, seeing, and being seen.

Here, in the central town square, you'll find the 13th-century Palazzo Pretorio, which has a facade adorned with coats of arms of Sovana's captains of justice, and the Renaissance Palazzo Bourbon dal Monte.

Here's where the ancient Roman amphitheater once stood. Some of the medieval buildings built over the amphitheater retain its original oval shape and brick arches.

With its irregular shape and sloping brick pavement, framed by buildings of assorted centuries, Arezzo's central piazza echoes Siena's Piazza del Campo. Though not quite so magnificent, it's lively enough during the outdoor antiques fair the first weekend of the month and when the Giostra del Saracino (Saracen Joust), featuring medieval costumes and competition, is held here on the third Saturday of June and on the first Sunday of September.

Filled with handsome buildings, this large square on the heights of the old historic town is Montepulciano's pièce de résistance.

Greve's gently sloping and asymmetrical central piazza is surrounded by an attractive arcade with shops of all kinds. In the center stands a statue of the discoverer of New York harbor, Giovanni da Verrazzano (circa 1480–1527). Check out the lively market held here on Saturday morning.

Ancient even by Chianti standards, this hilltop church probably dates from the 10th century, but it was completely rebuilt in the Romanesque style sometime in the 13th century. It has a 14th-century cloister worth seeing. The 16th-century terra-cotta tabernacles are attributed to Giovanni della Robbia, and there's also a remarkable triptych (attributed to the Master of Panzano) that was executed sometime in the mid-14th century. Open days and hours are unpredictable; check with the tourist office in Greve in Chianti for the latest information.

Even if a good portion of the arch was rebuilt by the Romans, three dark, weather-beaten, 4th-century-BC heads (thought to represent Etruscan gods) still face outward to greet those who enter here. A plaque on the outer wall recalls the efforts of the locals who saved the arch from destruction by filling it with stones during the German withdrawal at the end of World War II.

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.

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.

If you want to see more of that quintessential Tuscan landscape, walk up to the Rocca di Montestaffoli, which sits at the highest point in San Gimignano. Built after the Florentine conquest to keep an eye on the town, and dismantled a few centuries later, it's now a public garden.