This atmospheric 800-year-old palazzo near Piazza Grande, passed down through the innkeeper’s family, just doesn’t stop laying on the charm—in the arcaded, mosaic-filled courtyard; the vast, antiques-and-art-filled salon and breakfast room; the homey lounge; or the rooftop terrace that overlooks the checkerboard landscapes of the Valdichiana far below the town. Some rooms do justice to the surroundings with palatial expanses and view-filled terraces of their own, while others are simpler and viewless but not without charm—look for the replicas of carved wooden ricci, hedgehogs, that once emblazoned the 13th-century facade. Ivana and Giorgio Caroti are on hand to dispense advice and make restaurant reservations, and they serve delicious homemade pastries at breakfast and drinks throughout the day.