3 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.

This Romanesque abbey has been owned by internationally acclaimed cookbook author Lorenza de' Medici's family for more than a century and a half (the family isn't related to the Florentine Medici). Wine has been produced here since the abbey was founded by Vallombrosan monks in the 11th century. Today, the family continues the tradition, making wines, cold-pressed olive oil, and various flavored vinegars. Don’t miss the jasmine-draped courtyard and the inner cloister with its antique well.

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.