Cypress trees and stone walls encircle this historic 11th-century castle like a parapet in the Grosseto countryside. Fall into the rhythms of Tuscan life with a cooking class in the stone-arched kitchen, a hand in the grape or olive harvest, and a rooftop wine tasting as the sun sets. A full staff tends to the infinity pools, gazebo, gardens, and hiking trails, and Siena is a 75-minute drive.