Don’t miss the graffiti scrawled on the walls by war prisoners at the 900-year-old Torre Prendiparte (from $508), in Bologna. Once home to owner Matteo Giovanardi, the single, earth-toned room has a vaulted wood ceiling and is furnished with family heirlooms. Above the suite, there’s a whitewashed kitchen where you can fix your own meals.
In the Cinque Terre National Park, the nine-room La Torretta (doubles from $173) combines antique furnishings with kitschy details: light fittings crafted from antlers; bathrooms with starlit ceilings. The best part? Panoramic views of the turquoise Mediterranean from your bedroom window.
Architects Elisabetta Tovo and Filippo Cornero mix the contemporary and the classic at the one-room B&B Rotarius (from $406). Inside the 554-square-foot suite, you’ll find arched doorways, an ebony upright piano, and gilt-framed mirrors hanging on brick walls. A private terrace on the top level overlooks the Old Town’s center.
Medieval Modernism sets the scene at Torre di Moravola (doubles from $404), a 10th-century tower 25 minutes from Perugia. The seven suites are outfitted with Moroso armchairs and sunken stone baths; five have floating steel staircases. One caveat: the hotel is hard to find, so bring a map.