Situated 35 miles from Castiglione del Bosco, Arezzo is a favorite stop on many people’s itineraries. Head here to access Cathedral of Saints Peter and Donato and Basilica of San Francesco, a couple of terrific attractions to circle on your map. Nothing says living large like a road trip does, so keep on cruising to Perugia. It’s 50 miles away and also features a few rewarding sights, such as Piazza IV Novembre and Rocca Paolina.