GETTING OFF THE BEATEN PATH
Pitigliano is a hidden gem. It's a stunning hilltop town in southern Tuscany filled with cobblestone streets, winding staircases, and stone homes. Thankfully, it's off the well-beaten tourist path, perhaps because it's harder to get to without a car. We stayed at a beautiful Airbnb in the Jewish Quarter and to our happy surprise, the Airbnb host Federico made us the kind of breakfast that we wished we ate every morning (warm croissants, homemade jam, and fresh orange juice... yes please). He also gave us great tips about what to do in the area.
There were 2 parts of Pitigliano that really stood out for us. First, they have these ancient Etruscan roadways that we hiked for miles. These hillside roads (also called "via cava" or "vie cave") were carved into rock, which made the hike feel like a stone bobsled run. The second highlight was their annual wine festival. Local wineries open up their cave-like storage spaces, and serve wine to the locals wandering around the city after dark. We didn't know this was happening and lucked out to experience this special festival.