16 Best Sights in Tuscany, Italy

Tuscany's most-visited abbey sits in an oasis of olive and cypress trees amid the harsh landscape of Le Crete. It was founded in 1313 by Giovanni Tolomei, a rich Sienese lawyer who, after miraculously regaining his sight, changed his name to Bernardo in homage to St. Bernard of Clairvaux. Bernardo then founded a monastic order dedicated to the restoration of Benedictine principles. The name of the order—the White Benedictines—refers to a vision that Bernardo had in which Christ, Mary, and his own mother were all clad in white. The monks are also referred to as Olivetans (the name of the hill where the monastery was built).

In the abbey's main cloister, frescoes by Luca Signorelli and Sodoma depict scenes from the life of St. Benedict. Signorelli began the cycle by painting scenes from the saint's adult life as narrated by St. Gregory the Great. Though these nine scenes are badly worn, the individual expressions pack some punch. Later, Sodoma completed scenes from the saint's youth and the last years of his life. Note the detailed landscapes, the rich costumes, and the animals (similar to those Sodoma was known to keep as pets).

An imposing bishop's palace holds this unique museum of Etruscan objects. Although there are many beautiful pieces displayed in an intelligent and well-documented fashion, the almost complete roof and pediment from a 5th-century BC Etruscan house stand out as rare and precious. The so-called Cowboy of Murlo, a large-hatted figure from the same roof, is the star of the collection but anyone interested in ancient Etruscan culture will be well rewarded by a visit here. The museum is named after the nearby site from which most of the artifacts were excavated.

The famous Piero della Francesca frescoes depicting The Legend of the True Cross (1452–66) were executed on the three walls of the Capella Bacci, the apse of this 14th-century church. What Sir Kenneth Clark called "the most perfect morning light in all Renaissance painting" may be seen in the lowest section of the right wall, where the troops of Emperor Maxentius flee before the sign of the cross. Reservations are required and can be made online.

If you have time for only one castle in Tuscany, this is it. At the end of the 12th century, when Florence conquered southern Chianti, Brolio became Florence's southernmost outpost, and it was often said, "When Brolio growls, all Siena trembles." It was built about AD 1000 and owned by the monks of the Badia Fiorentina. The "new" owners, the Ricasoli family, have been in possession since 1141. Bettino Ricasoli (1809–80), the so-called Iron Baron, was one of the founders of modern Italy and is said to have invented the original formula for Chianti wine.

Brolio, one of Chianti's best-known labels, is still justifiably famous. The grounds are worth visiting, and some of the guided tours do provide a glimpse of the castle's interior. The entrance fee includes a wine tasting in the enoteca. A small museum, where the Ricasoli Collection is housed in a 12th-century tower, displays objects that relate the long history of the family and the origins of Chianti wine. There are various options for an overnight here.

The town's main church is not officially a duomo (cathedral), because San Gimignano has no bishop. But behind the simple facade of the Romanesque Collegiata lies a treasure trove of fine frescoes, covering nearly every wall. Bartolo di Fredi's 14th-century fresco cycle of Old Testament scenes extends along one wall. Their distinctly medieval feel, with misshapen bodies, buckets of spurting blood, and lack of perspective, contrasts with the much more reserved scenes from the Life of Christ (attributed to 14th-century artist Lippo Memmi) painted on the opposite wall just 14 years later.

Routine excavation work revealed this crypt, which had been hidden for centuries under the grand pavimento (floor) of the Duomo and was opened to the public in 2003. In the late 13th century, an unknown master executed the crypt's breathtaking frescoes, which have sustained remarkably little damage and have retained their original colors. The Deposition/Lamentation proves that the Sienese school could paint emotion just as well as the Florentine school—and that it did so some 20 years before Giotto.

Siena's cathedral is one of the finest Gothic churches in Italy. The multicolored marble and painted decoration are typical of the Italian approach to Gothic architecture—lighter and much less austere than the French. The amazingly detailed facade has few rivals. It was completed in two brief phases at the end of the 13th and 14th centuries. The statues and decorative work were designed by Nicola Pisano and his son Giovanni, although much of what's seen today are copies, the originals having been removed to the adjacent Museo dell'Opera Metropolitana. The gold mosaics are 18th-century restorations. The campanile (no entry) is among central Italy's finest, the number of windows increasing with each level, a beautiful and ingenious way of reducing the weight of the structure as it climbs to the heavens.

With its dark-green-and-white striping throughout and its illusionistic coffered and gilded dome, the Duomo's interior is simply striking. Look up at copies of Duccio's (circa 1255–1319) stained-glass panels; the originals, finished in 1288, are in the Museo dell'Opera and are among the oldest examples of stained glass in Italy. The Duomo is most famous, though, for its inlaid-marble floors, which took almost 200 years to complete. More than 40 artists contributed to the magnificent work of 56 compositions depicting biblical scenes, allegories, religious symbols, and civic emblems. Although conserving the floors requires keeping them covered for much of the year, they are unveiled from the end of June until the end of July and from mid-August until mid-October.

Also noteworthy is the Duomo's carousel pulpit, carved by Nicola Pisano around 1265; the Life of Christ is depicted on the rostrum frieze. In striking contrast to the nave's Gothic decoration are the well-preserved Renaissance frescoes in the Biblioteca Piccolomini, off the left aisle. Painted by Pinturicchio (circa 1454–1513) and completed in 1509, they depict events from the life of Aeneas Sylvius Piccolomini (1405–64), who became Pope Pius II in 1458.

The Duomo is grand, but the medieval Sienese people had even grander plans, namely, to use the existing church as a transept and build a new nave running toward the southeast, creating what would have been the world's largest church. Alas, only the side wall and part of the new facade were completed when the Black Death struck in 1348. The city subsequently fell into decline, funds dried up, and the plans were never carried out.

Indeed, the grand church project was actually doomed from the start—subsequent attempts to get it going revealed that the foundation was insufficient to bear the weight of the proposed structure. In any event, the unfinished new nave extending from the right side of the Duomo was ultimately enclosed to house the Museo dell'Opera. The Cripta was discovered during routine preservation work on the church.

Providing refuge for the last remnants of the Sienese army during the Florentine conquest of 1555, the battlements of this 14th-century fortress are still in excellent condition. Climb the narrow, spiral steps for the 360-degree view of most of southern Tuscany. An on-site enoteca serves delicious snacks that pair beautifully with the local wines.

Legend holds that Galileo conducted an experiment on the nature of gravity by dropping metal balls from the top of the 187-foot-high Leaning Tower of Pisa. Historians, however, say this legend has no basis in fact—which isn't quite to say that it's false. Work on this tower, built as a campanile (bell tower) for the Duomo, started in 1173. The lopsided settling began when construction reached the third story.

The architects attempted to compensate through such methods as making the remaining floors slightly taller on the leaning side, but the extra weight only made the problem worse. The settling continued, and, by the late 20th century, it had accelerated to such a point that many feared the tower would simply topple over, despite all efforts to prop it up. The structure has since been firmly anchored to the earth. Work to restore the tower to its original tilt of 300 years ago was launched in early 2000 and finished two years later. This involved removing some 100 tons of earth from beneath the foundation.

Reservations, which are essential, can be made online or by calling the Museo dell'Opera del Duomo. It's also possible to arrive at the ticket office and book for the same day. Note, though, that children under eight aren't allowed to climb.

Palazzo Corboli, a magnificent palace dating from the 12th century, has been refurbished and houses the Museo d'Arte Sacra e Archeologico. The collection of Etruscan artifacts is worth a visit, though the real highlight is the collection of lesser-known 13th- and 14th-century paintings from the Sienese school.

Part of the unfinished nave of what was to have been a new cathedral, the museum contains the Duomo's treasury and some of the original decoration from its facade and interior. The first room on the ground floor displays weather-beaten 13th-century sculptures by Giovanni Pisano (circa 1245–1318) that were brought inside for protection and replaced by copies, as was a tondo of the Madonna and Child (now attributed to Donatello) that once hung on the door to the south transept.

The masterpiece is unquestionably Duccio's Maestà, one side with 26 panels depicting episodes from the Passion, the other side with a Madonna and Child Enthroned. Painted between 1308 and 1311 as the altarpiece for the Duomo (where it remained until 1505), its realistic elements, such as the lively depiction of the Christ child and the treatment of interior space, proved an enormous influence on later painters. The work originally decorated the Duomo's high altar before being displaced by Duccio's Maestà. There is a fine view from the tower inside the museum.

An extraordinary collection of Etruscan relics is made all the more interesting by clear explanations in English. The bulk of the collection is comprised of roughly 700 carved funerary urns. The oldest, dating from the 7th century BC, were made from tufa (volcanic rock). A handful are made of terra-cotta, but most—dating from the 3rd to 1st century BC—are done in alabaster. The urns are grouped by subject, and, taken together, they form a fascinating testimony about Etruscan life and death.

On nice days, the citizens of Lucca cycle, jog, stroll, or kick a soccer ball in this green, beautiful, and very large circular park. It's neither inside nor outside the city but rather right atop and around the ring of ramparts that defines Lucca. Sunlight streams through two rows of tall plane trees to dapple the passeggiata delle mura (walk on the walls), which is 4 km (2½ miles) long. Ten bulwarks are topped with lawns, many with picnic tables and some with play equipment for children. Be aware at all times of where the edge is—there are no railings, and the drop to the ground outside the city is a precipitous 40 feet.

The fan-shaped Piazza del Campo, known simply as Il Campo (The Field), is one of the finest squares in Italy. Constructed toward the end of the 12th century on a market area unclaimed by any contrada, it's still the heart of town. Its brickwork is patterned in nine different sections—representing each member of the medieval Council of Nine.

At the top of the Campo is a copy of the early 15th-century Fonte Gaia by Siena's greatest sculptor, Jacopo della Quercia. The 13 sculpted reliefs of biblical events and virtues that line the fountain are 19th-century copies; the originals are in the museum complex of Santa Maria della Scala. On Palio horse-race days (July 2 and August 16), the Campo and all its surrounding buildings are packed with cheering, frenzied locals and tourists craning their necks to take it all in.

Designed by Antonio da Sangallo il Vecchio, and considered his masterpiece, this church sits on the hillside below the town walls and is a model of High Renaissance architectural perfection. Inside is a painting of the Madonna that, according to legend, was the only thing remaining in an abandoned church that two young girls entered on April 23, 1518. The girls saw the eyes of the Madonna moving, and that same afternoon so did a farmer and a cow, who knelt down in front of the painting. In 1963, the image was proclaimed the Madonna del Buon Viaggio (Madonna of the Good Journey), the protector of tourists in Italy.

For more than 1,000 years, this complex across from the Duomo was home to Siena's hospital, but it now serves as a museum containing, among other things, Sienese Renaissance treasures. Restored 15th-century frescoes in the Sala del Pellegrinaio (once the emergency room) tell the history of the hospital, which was created to give refuge to passing pilgrims and others in need and to distribute charity to the poor. Incorporated into the complex is the church of the Santissima Annunziata, with a celebrated Risen Christ by Vecchietta (also known as Lorenzo di Pietro, circa 1412–80). Down in the dark, Cappella di Santa Caterina della Notte is where St. Catherine went to pray at night.

The displays—including the bucchero (dark, reddish clay) ceramics, Roman coins, and tomb furnishings—are clearly marked and can serve as a good introduction to the history of regional excavations. Be sure to visit the subterranean archaeological museum to see della Quercia's original sculpted reliefs from the Fonte Gaia. Although the fountain has been faithfully copied for the Campo, there's something incomparably beautiful about the real thing.