Castello del Trebbio

Castello del Trebbio hosts everything from a winery to a restaurant (and cooking classes) to accommodations. It's hard to pin down just what visitors like most about the experience. One TripAdvisor user says, "It is a family-run winery that places high importance on quality wine and excellent olive oil." Others say the 12th-century castle's ambience is the coolest, while some find tasting different Chianti vintages and learning to make Italian pastas to be the most satisfying things about this estate winery.

And here's an interesting historic tidbit: This castle was once owned by the Pazzi family, the arch enemies of another powerful Italian family, the Medicis. You'll find this winery on the outskirts of Florence. For more information, visit its website.