We've rented out an entire 12th century medieval tower in San Gimignano!
We start in Lucignano, a tiny Tuscan town shaped like a wedding cake in three concentric circles. For about $60/night, we stay inside the town's walls in a small B&B, whose walls are adorned with beautiful murals.
Then it's on to San Gimignano, "Manhattan of the Middle Ages", in Tuscany. So called for its multiple famous medieval towers. For three nights, we're renting a tower to live in -- all 11 stories. It's 160 steps up to the top, which is now a panoramic terrace. It's a stunning town, and this is truly unique place to stay.
We finish in Castel Gandolfo, just south of Rome. This town, perched on the side of a cliff overlooking a lake, is the summer home of the Pope. For about $100/night we're staying in the middle of town. It's a very small, lake resort town, kind of too beautiful to believe.