Most famous for its excellent Brunello di Montalcino wines, the hilltop town of Montalcino is the perfect place to enjoy a leisurely lunch after visiting one of the surrounding wineries. (Big names like Ruffino, Antinori, and Banfi all have estates here.) Head to Ristorante Enoteca Osticcio, a wine shop with a few tables in a small dining room with panoramic views of the Tuscan hills, for local specialties paired with a glass of one of the area’s signature reds. Stroll through the medieval streets and piazzas lined with shops selling everything from leather goods to local olive oil. Stay at Castello di Velona, known for its thermal spa and pool overlooking the scenic Val d’Orcia.

RELATED: 8 Wine-Friendly Spas Where You Can Booze and Beautify