The taller your tower in medieval Italy, the more powerful your family was. Height not only meant higher stature, but also protection. San Gimignano is a well-preserved Italian town in the Tuscan valley where you can still see this medieval cityscape. The town has some of the best gelato in Tuscany, as well as bed and breakfasts and great views. Traveling from New York City, I took particular delight in this humble, storied town.