17 Best Sights in Arezzo, Cortona, and Eastern Tuscany, Tuscany

Periodic excavations since 1950 have brought to light segments of Arezzo's Roman amphitheater, which was probably built during the early 2nd century AD. The entire perimeter has been exposed, and you can see some of the entrance passages and the structures that supported the amphitheater's central arena. The ticket price includes admission to the Museo Archeologico.

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.

Giorgio Vasari (1511–74), the region's leading Mannerist artist, architect, and art historian, designed and decorated this house after he bought it in 1540. He ended up not spending much time here, since he and his wife moved to Florence in 1554. Today, the building houses archives on Vasari, as well as works by the artist and his peers. In the first room, which Vasari called the "Triumph of Virtue Room," a richly ornamented wooden ceiling shows Virtue combating Envy and Fortune in a central octagon.

Cortona's cathedral stands on an edge of the city, next to what's left of the Etruscan and medieval walls. Built on the site of a Romanesque church, the present Renaissance church was begun in 1480 and finished in 1507. An arcade along the outside wall was erected in the 16th century. The interior, a mixture of Renaissance and baroque styles, features an exquisite 1664 baroque tabernacle on the high altar by Francesco Mazzuoli.

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.

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.

Piero della Francesca is the star at this small provincial museum, where his works include the reassembled altarpiece of the Misericordia (1445–62) and frescoes depicting the Resurrection (circa 1460), Saint Julian, and the disputed Saint Louis of Toulouse, which is possibly the work of a close follower of the artist. Other works of interest are those by Santi di Tito (1536–1603), also from Sansepolcro, and Pontormo's San Quintino (1517–18).

Not surprisingly, only one painting is displayed here, Piero's Madonna del Parto (circa 1455), a fresco depicting the expectant Virgin flanked by two angels. Originally painted for the small chapel of Santa Maria a Momentana in Monterchi's cemetery, the work was restored in 1992–93 and moved, shortly thereafter, into the museum. The iconography of the image is extremely rare and, emphasized by its static atmosphere and studied symmetry, the fresco achieves an extraordinary sense of enigmatic and monumental spirituality.

Opened in 1964 to honor the 400th anniversary of Michelangelo's death, the museum displays photographs, plaster casts, and documents relating to the artist's work.

Built by the Casali family, who lived here until 1409, this palace is home to the Accademia Etrusca, with an extensive library, La Biblioteca Comunale, and the Museo dell'Accademia Etrusca e della Città di Cortona (aka MAEC). An eclectic mix of Egyptian objects, Etruscan and Roman bronzes and statuettes, and paintings is on display in the museum. Perhaps the most famous piece is the Tabula Cortonensis, an Etruscan contract written on bronze that was found in 1922 and dates from the second century BC. Look for work by Renaissance artists such as Luca Signorelli and Pinturcchio (circa 1454–1513). From May through September, guided tours are available in English with prior arrangement.

In 1012, four centuries after the founding of the Benedictine order, St. Romualdo—feeling that his order had become too permissive—came to the forests of the Casentino and found their remoteness, beauty, and silence more conducive to religious contemplation. He stayed and founded this hermitage, which was named for Count Maldoli, who donated the land, and which became the seat of a reformed Benedictine order. An important requirement of the new order was preserving its 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.

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 century). Among the other works is a Madonna and Child by Luca Signorelli.

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.

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 the 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.

The large 1897 basilica was constructed over the foundation of a 13th-century church dedicated to the same saint. What makes the 10-minute uphill walk worthwhile is the richly decorated interior. The body of the 13th-century St. Margherita—clothed but with skull and bare feet clearly visible—is displayed in a case on the main altar.

A few hills away from the Monastero di Camaldoli, dramatically perched on a sheer-walled rock surrounded by firs and beeches, is La Verna, founded by St. Francis of Assisi in 1214. Ten years later, after a 40-day fast, St. Francis had a vision of Christ crucified, and when it was over, Francis had received the stigmata, the signs of Christ's wounds, on his hands, feet, and chest. A stone in the floor of the 1263 Chapel of the Stigmata marks the spot.

A covered corridor through which the monks pass, chanting in a solemn procession each day at 3 pm on the way to Mass, is lined with simple frescoes of the Life of St. Francis by a late-17th-century Franciscan artist. The true artistic treasures of the place, though, are 15 della Robbia glazed terra-cottas. Most, like a heartbreakingly beautiful Annunciation, are in the 14th- to 15th-century basilica, which has a 5,000-pipe organ that sings out joyously at Masses.

Several chapels, each with its own story, can be visited, and some natural and spiritual wonders can also be seen. A walkway along the 230-foot-high cliff leads to an indentation where the rock is said to have miraculously melted away to protect St. Francis when the devil tried to push him off the edge. Most touching is the enormous Sasso Spicco (Projecting Rock), detached on three sides and surrounded with mossy rocks and trees, where St. Francis meditated. You can also view the Letto di San Francesco (St. Francis's Bed), a slab of rock in a cold, damp cave with an iron grate on which he prayed, did penance, and sometimes slept.

A 40-minute walk through the woods to the top of Mt. Penna passes some religious sites and ends in panoramic views of the Arno Valley, but those from the wide, cliff-edge terrace are equally impressive, including the tower of the castle in Poppi, the Prato Magno (great meadow), and the olive groves and vineyards on the lower slopes. Santuario della Verna's foresteria also has simple but comfortable rooms with or without bath. A restaurant with basic fare is open to the public, and a shop sells souvenirs and the handiwork of the monks.

As you leave La Verna, be glad you needn't do it as Edith Wharton (1862–1937) did on a 1912 visit during a drive across the Casentino. As she wrote, her car "had to be let down on ropes to a point about ¾ mile below the monastery, Cook [her chauffeur] steering down the vertical descent, and twenty men hanging on to a funa [rope] that, thank the Lord, didn't break."