Sarteano

Small Sarteano sits on a hilltop above plains scattered with wineries and rustic farms. It’s marked out by its colossal castle, which sprouts from a forest over the narrow alleys and steeply sloping streets below. After scrambling to the bulwarks and drawbridge in the citadel, you can head back to the main piazza to reward yourself with a stacked gelato and coffee. On weekends, a rural market erupts in the center. It’s a people watching mecca, filled with stalls scented with wild porcini mushrooms and pecorino cheeses.