42km (26 miles) NW of Siena; 52km (32 miles) SW of Florence; 270km (168 miles) NW of Rome

Let’s just get the clichés out of the way, shall we?—“Manhattan of the Middle Ages” and “City of Beautiful Towers.” There, it’s said. As every brochure will tell you, in the 12th and 13th centuries more than 70 towers rose above the tile roofs of San Gimignano, built partly to defend against outside invaders but mostly as command centers and status symbols for San Gimignano’s powerful families. A dozen towers remain, and as you approach across the rolling countryside, they do indeed appear like skyscrapers, giving the town the look of a fantasy kingdom. Once inside the gates, the Manhattan reference seems all too apt, with visitors shoulder-to-shoulder in its narrow lanes, obliterating the medieval aura you’ve come to savor. Almost everyone traveling the hilltown circuit makes a stop here, while bus tours pour in from Siena and Florence, and Italians arrive on weekend outings. If you want to be swept back to the Middle Ages, you’re best visiting midweek in off-season, or late on weekday afternoons after the buses have headed home.