3 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.

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.