San Gimignano

When you're on a hilltop surrounded by soaring medieval towers silhouetted against the sky, it's difficult not to fall under the spell of San Gimignano. Its tall walls and narrow streets are typical of Tuscan hill towns, but it's the medieval "skyscrapers" that set the town apart from its neighbors. Today 14 towers remain, but at the height of the Guelph-Ghibelline conflict there was a forest of more than 70, and it was possible to cross the town by rooftop rather than by road. The towers were built partly for defensive purposes—they were a safe refuge and useful for pouring boiling oil on attacking enemies—and partly for bolstering the egos of their owners, who competed with deadly seriousness to build the highest tower in town.

Today San Gimignano isn't much more than a gentrified walled city, touristy but still very much worth exploring because, despite the profusion of cheesy souvenir shops lining the main drag, there's some serious Renaissance art to be seen here. Tour groups arrive early and clog the wine-tasting rooms—San Gimignano is famous for its light white Vernaccia—and art galleries for much of the day, but most sights stay open through late afternoon, when all the tour groups have long since departed.