With its tower-filled skyline and well-preserved medieval buildings that earned it a UNESCO World Heritage designation, San Gimignano is one of Tuscany’s most beautiful hilltop towns (as well as its most famous). If you think its 14 standing towers are impressive, however, wait until you hear the whole story: back during ancient times, rival families built taller and taller towers as a sign of their personal wealth. At one time, there were as many as 72 towers in town, which pilgrims could spot from miles away. Today, the 14 that still stand share their streets with the 15th-century Church of Sant’Agostino and 12th-century Collegiate Church of Santa Maria Assunta—both known for their ancient frescoes—as well as one of Italy’s best artisanal ice cream shops (go for the rosemary or lavender).