Just as Pope Pius introduced the latest in Renaissance fashion to little Pienza, this stylish guesthouse does the same with 21st-century decor. Huge, loftlike guest quarters seem better suited to New York or Berlin (the elevator is the only one for miles around), but they certainly prove that contemporary chic can be comfortable. Amid design-magazine staples like steel frame beds, distressed leather armchairs, and slinky divans, you can enjoy luxuries you might not have at home, such as slipping effortlessly from a supremely comfortable mattress into a deep tub perched right alongside. Timeless pleasures include honey-colored stone walls and garden views over the surrounding countryside. The dining room, furnished with retrofitted furnishings from a 1950s-era Florence school, sticks to straightforward takes on local cuisine, with innovations that include hamburgers made from the best Valdichiana beef.