5Pitigliano

Located in a less-traveled part of Tuscany, this town can only be accessed by bus or car (there’s no train service). But that only makes it more of an undiscovered gem. Once you are in Pitigliano, you can easily see it all on foot. Head to the tourist office and ask about tours of the underground tunnels, caves, and tombs.

You’ll even see a Christian cave chapel dating to 400 AD. The 14th-century Palazzo Orsini (The Orsini family was one of several who held sway here over the centuries) is now a museum where you can see a variety of artwork and relics as well as a medieval torture chamber. The ancient Jewish quarter, empty since shortly after WWII, is also open to the public.