Both picturesque and formidable, the 14 towers of San Gimignano loom over the city’s small piazze and meandering walls. The towers date back to a period when prosperous families used the town square as their personal battlefield. During sieges, they were a handy vantage point for dumping boiling oil on neighbors. Nowadays there’s very little need for scalding fluids, as San Gimignano’s impressive skyline and the region’s dry white Vernaccia wine draw nothing more dangerous than tourists by the busload—30 buses a day from Poggibonsi, to be precise.

You will never see so many older folk chugging their way up steep hills as you will in this town. V. San Giovanni is congested with tourists and tourist schlock, and you can hardly move for fear of stepping into a photograph or onto a Pinocchio doll. Luckily, San Gimignano’s infernal verticality means that the crowds rarely wander off the very beaten path—you need only walk a few meters down (more likely up) a side street to be completely alone. Strap your feet into some walking shoes and explore the towers of San Gimignano from the outside in.