San Gimignano is the epitome of a Tuscan hill town. About 25 miles from both Florence and Siena, it's the region's glamour girl: Visually striking and perfectly preserved, it gets all the fawning attention from passing tour buses. But despite its tourist-trap feel, it's still worth slotting into your Italian itinerary — especially if you can sidestep the hordes who descend during the day.
San Gimignano is beloved because of its skyline of medieval towers. Though a unique sight today, pointy skylines were the norm in Tuscany in the Middle Ages, when feuding noble families ran the hill towns (think Montagues and Capulets). Each family had its own private army that would periodically battle things out from the protection of its respective family towers. While some were built as a refuge against attackers, others were empty, chimney-like structures built only to boost noble egos.
In the 14th century, San Gimignano, like other hill towns, fell under Florence's control. The Florentines usually asserted their power over the local nobles by ordering them to lop off their towers. But for whatever reason, some of San Gimignano's original skyline was allowed to remain intact. Today, 14 of its original 72 towers still stand.
