210 Best Sights in Tuscany, Italy

The superb collection of five centuries of local painting in Siena's national picture gallery can easily convince you that the Renaissance was by no means just a Florentine thing. Accordingly, the most interesting section of the collection, chronologically arranged, has several important firsts. Room 1 contains a painting of the Stories of the True Cross (1215) by the so-called Master of Tressa, the earliest identified work by a painter of the Sienese school, and is followed in Room 2 by late-13th-century artist Guido da Siena's Stories from the Life of Christ, one of the first paintings ever made on canvas (earlier painters used wood panels).

Rooms 3 and 4 are dedicated to Duccio, a student of Cimabue (circa 1240–1302) and considered to be the last of the proto-Renaissance painters. Ambrogio Lorenzetti's landscapes in Room 8 are among the first truly secular paintings in Western art. Among later works in the rooms on the floor above, keep an eye out for the preparatory sketches used by Domenico Beccafumi (1486–1551) for the 35 etched marble panels he made for the floor of the Duomo.

For a look at gracious country living Renaissance style, take a detour to the Medici villa in Poggio a Caiano. Lorenzo "il Magnifico" (1449–92) commissioned Giuliano da Sangallo (circa 1445–1516) to redo the villa, which was lavished with frescoes by important Renaissance painters such as Pontormo (1494–1556), Franciabigio (1482–1525), and Andrea del Sarto (1486–1531). You can walk around the austerely ornamented grounds while waiting for one of the villa tours, which start on the half hour. The guides do not speak; rather, they follow you around the place.

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.

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 Monte Argentario's north side, busy and colorful Porto Santo Stefano is the peninsula'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.

Bagno Vignoni's main hot-spring pool is inside the luxury Posta Marcucci Spa hotel. Non-hotel guests can swim in the three outdoor pools, which range in temperature from 38°C (100°F) to 28°C (82°F), and can use the sun beds and umbrellas in the garden. Slippers and bathing caps are compulsory and can be purchased at the ticket desk. Entry is more expensive on the weekends.

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.

At this family-run and -operated establishment, you can do a simple wine tasting, or taste while eating lunch or dinner at the rather fine restaurant. It's also possible to stay on the estate in restored farmhouses.

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.

An important requirement at this hermitage, founded by St. Romualdo in the 11th century for the reformed Benedictine order, was preserving an ascetic atmosphere: "If the hermits are to be true devotees of solitude, they must take the greatest care of the woods." When the flow of pilgrims began to threaten that solitude, Romualdo had a monastery and hospital built down the mountain to create some distance.

Today, you can view the hermitage—where the monks live in complete silence in 20 separate little cottages, each with its own walled garden—through gates and visit the church and original cell of Romualdo, the model for all the others. The church, rebuilt in the 13th century and transformed in the 18th to its present appearance, strikes an odd note in connection with such an austere order and the simplicity of the hermits' cells, because it's done up in gaudy baroque style, complete with gilt cherubs and a frescoed vault. Its most appealing artwork is the glazed terra-cotta relief Madonna and Child with Saints (including a large figure of Romualdo and a medallion depicting his fight with the devil) by Andrea della Robbia. The main entrance to the hermitage, the bronze Porta Speciosa (Beautiful Door) of 2013, by Claudio Parmiggiani (born in 1943), has an inscription on its inner side that likens the monks' spirits to the trees that they tend.

Within the Monastero di Camaldoli, 3 km (1 mile) away, is a church (repeatedly restructured) containing 14th-century frescoes by Spinello Aretino, seven 16th-century panel paintings by Giorgio Vasari, and a quietly lovely monastic choir. The choir has 18th-century walnut stalls, more Vasari paintings, and a serene fresco (by Santi Pacini) of St. Romualdo instructing his white-robed disciples. In a hospital built for sick villagers in 1046, the 1543 Antica Farmacia (Old Pharmacy) contains original carved walnut cabinets. Here you can buy herbal teas and infusions, liqueurs, honey products, and toiletries made by the monks from centuries-old recipes as part of their daily routine balancing prayer, work, and study (the monastery is entirely self-supporting). In the back room is an exhibit of the early pharmacy's alembics, mortars, and other equipment with which the monks made herbs into medicines. You can attend short spiritual retreats organized by the monks throughout the year; contact the foresteria (visitors lodge) for details.

During two weekends in mid-October, Caprese Michelangelo's very lively Sagra della Castagna takes place. Among the many other chestnut-based 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.

Inside the northern city walls, this church was begun by Dominican friars in 1275 and completed in the 14th century. The walls were once completely frescoed and decorated with niches and chapels. Very little remains of the original works, but a famous 13th-century crucifix by Cimabue (circa 1240–1302) and frescoes by Spinello Aretino (1350–1410) still survive.

Although the Duomo is celebrated as a triumph of 13th-century Gothic architecture, this church, built at about the same time, turned out to be an oversize, hulking brick box that never merited a finishing coat in marble, let alone a graceful facade. Named for the founder of the Dominican order, the church is now more closely associated with St. Catherine of Siena. Just to the right of the entrance is the chapel in which she received the stigmata. On the wall is the only known contemporary portrait of the saint, made in the late 14th century by Andrea Vanni (circa 1332–1414). Farther down is the famous Cappella delle Santa Testa, the church's official shrine.

On either side of the chapel are well-known frescoes by Sodoma (aka Giovanni Antonio Bazzi, 1477–1549) of St. Catherine in Ecstasy. Don't miss the view of the Duomo and town center from the apse-side terrace.

Inside this rather nondescript 14th-century church, just outside Cortona's walls, is an altarpiece depicting the Coronation of the Virgin against a sparkling gold background by Lorenzo di Niccolò Gerini (active late 14th–early 15th centuries). Among the other works is a Madonna and Child by Luca Signorelli.

In the mid-13th century, this Gothic-style church was built on the site of Etruscan and Roman baths. It is decorated with frescoes that date from 1382 and a 17th-century crucifix by Giuseppe Piamontini of Florence. It also houses a relic of Santa Croce, a vestige of the True Cross apparently given to Brother Elia when he served as an envoy for Federico II in Constantinople. The church's rather beautiful organ was unfortunately badly damaged during World War II.

Look inside the church for the celebrated early-15th-century frescoes of the Legend of the True Cross by a local artist. It traces the history of the wood used to make the cross upon which Christ was crucified. From Piazza San Giovanni, take Via Franceschini (which becomes Via San Lino) to the church.

The lovely baroque church of San Francesco is a study in understated elegance. It dates from the 1620s to 1660s, and, even though it was built during the peak years of the baroque, the only excess can be found in the twisting marble columns embellishing the altars.

A 14th-century mosaic decorates the facade of this church just steps from the anfiteatro. Inside are works by Jacopo della Quercia and Matteo Civitali (1436–1501), as well as the lace-clad mummy of St. Zita (circa 1218–78), the patron saint of household servants.

An architectural gem in green-and-white marble, the medieval church of San Giovanni Fuorcivitas holds a Visitation by Luca della Robbia (1400–82), a painting attributed to Taddeo Gaddi, and a holy-water font that may have been made by Fra Guglielmo around 1270.

Built in the 1840s on a Greek-cross plan, this neoclassical church contains a Madonna and Child with angels by an anonymous 15th-century master. Also inside is the Holy Family with St. Catherine of Siena, attributed to Arcangelo Salimbeni (1530/40–79).

The oldest and most interesting of the hilltop medieval villages that surround Castelnuovo Berardenga retains its early 1400s layout, with arched passageways, gates topped with coats of arms, narrow squares, and steep streets. You can walk through the entire village in 20 minutes, but in those 20 minutes you may feel as if you have stepped back in time some 600 years.

Don't miss this small church, which houses a striking Annunciation by the important Sienese painter Domenico Beccafumi (1486–1551).

The facade here is even more fanciful than that of the Duomo. Its upper levels have nothing but air behind them (after the front of the church was built, there were no funds to raise the nave), and the winged archangel Michael, who stands at the very top, seems precariously poised for flight. The facade, heavily restored in the 19th century, displays busts of such Italian patriots as Garibaldi and Cavour. Check out the superb Filippino Lippi (1457/58–1504) panel painting of Saints Jerome, Sebastian, Rocco, and Helen in the right transept.

A short but not very scenic walk from the center of town brings you to the little church of San Michele in Pontorme, chiefly notable for the gorgeous St. John the Baptist and St. Michael the Archangel, two works dating from about 1519 by native son Jacopo Carrucci (1494–1556), better known as Pontormo. Opening hours are erratic, so it's best to check with the tourist information office to see what's what.

Built over remnants of two earlier churches is this 11th-century basilica, situated on the Arno about 8 km (5 miles) southwest of Pisa. According to legend, it was here that St. Peter the Apostle stepped off the boat in AD 42—his first step on Italian soil. (It would have made more sense for him to land on the Adriatic Coast, as he was coming from Antioch.)

The structure is a lovely example of Romanesque architecture, and it's not without its quirks: it has two apses, one at each end. On the walls are some crumbling, but still vibrant, frescoes dating from the 12th and 13th centuries. Thirty-one of these frescoes depict scenes from the lives of saints Peter and Paul, an uncommon subject in Tuscan wall painting. A car is a necessity to get to this lovely church.

Make a beeline for Benozzo Gozzoli's superlative 15th-century fresco cycle depicting scenes from the life of St. Augustine. The saint's work was essential to the early development of church doctrine. Benozzo's 17 scenes on the choir wall depict Augustine as a man who traveled and taught extensively in the 4th and 5th centuries. The 15th-century altarpiece by Piero del Pollaiolo (1443–96) depicts The Coronation of the Virgin and the various protectors of the city.

Michelozzo had a hand in creating the beautiful travertine facade on the church of Sant'Agostino, which was built in 1285 and renovated in the early 1400s. He also sculpted the terra-cotta relief of the Madonna and Child above the entrance.

In the 12th-century church of Sant'Andrea, the fine pulpit by Giovanni Pisano (circa 1250–1314) depicts scenes from the life of Christ in a series of high-relief, richly sculpted marble panels.