Borgo Vescine

Lined along a hillside hamlet in the Chianti Radda zone, Borgo Vescine gathers restored medieval stone buildings into a five-star retreat roughly 60km south of Florence — a natural base for guests touring Siena (30km) and the vine-terraced ridge roads between them.

The outdoor pool anchors the lower terrace; the restaurant runs themed dinners drawing on local produce, with cooking classes offered for guests who want the recipes to travel home. Bicycle rental and guided bike tours push the property further into the surrounding countryside, while horseback riding can be arranged through the concierge.

Rooms carry minibars, robes, and open-air baths in select configurations. The on-site massage menu spans back, neck, foot, and full-body treatments — a practical recovery option after a day in the saddle or on the hills.