7 Best Sights in Tuscany, Italy

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.

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.

This formidable structure, near Santa Maria delle Carceri, is an impressive sight. The (Sicilian) Holy Roman Emperor Frederick II (1194–1250) built the seat of his authority in Tuscany in this somewhat unlikely spot. Frederick's castles were designed to echo imperial Rome, and the many columns, lions, and porticoes testify to his ambition. This is the only castle he built outside southern Italy (other examples may be found in Sicily and Puglia).

The impressive civic museum occupies what was the "new" Palazzo del Popolo; the Torre Grossa is adjacent. Dante visited San Gimignano for only one day as a Guelph ambassador from Florence to ask the locals to join the Florentines in supporting the pope—just long enough to get the main council chamber named after him.

Upstairs, paintings by famous Renaissance artists Pinturicchio (Madonna Enthroned) and Benozzo Gozzoli (Madonna and Child), and two large tondi (circular paintings) by Filippino Lippi (circa 1457–1504) attest to the importance and wealth of San Gimignano.

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.

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.

In 1459, Pius II commissioned Bernardo Rossellino to design the perfect palazzo for his papal court. The architect took Florence's Palazzo Rucellai by Alberti as a model and designed this 100-room palace. Three sides of the building fit perfectly into the urban plan around it, while the fourth, looking over the valley, has a lovely loggia uniting it with the gardens in back. Guided tours departing every 30 minutes take you to the papal apartments, including a beautiful library, the Sala delle Armi (with an impressive weapons collection), and the music room, with its extravagant wooden ceiling forming four letter Ps, for Pope, Pius, Piccolomini, and Pienza. The last tour departs 30 minutes before closing.