5 Best Sights in Gaiole in Chianti, Tuscany

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.

One of Chianti Classico's top estates, Castello di Ama offers 90-minute visits that include a guided tour through the estate, a look at the historical cellar, and a tasting of three wines. Along the way, you'll see site-specific contemporary art installations created by artists from around the world. If you'd like to linger, stay the night in one of five suites in the 18th-century manor house, Villa Ricucci.

If you have time for only one castle in Tuscany, this should be 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; you can also visit the on-site Barone Ricasoli winery for a guided cellar tour and wine tasting.

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.

It's a pretty drive up winding roads to this 13th-century fortress. Attached is an 18th-century villa; a wineshop serves tastes of the locally produced wine as well as honeys and jams. It's worth visiting the castle, which is possible by guided-tour only (reservations required), to get a sense of how 18th-century aristocrats lived; the tour also includes a visit to the cellar and the gardens. If that doesn't interest you, proceed directly to the enoteca for a tasting. Apartments clustered near the castle are available for rent.

Dating from the 10th century, this walled town is oval in shape and has a tall watchtower guarding the entrance gate. A walk along the unspoiled streets gives you a glimpse of life in a Tuscan hill town as it once was, and the views of the undulating countryside from the occasional opening in the walls are simply spectacular.