32 Enchanting Medieval Towns That Feel Frozen in Time

6. San Gimignano, Italy

San Gimignano, often referred to as the "Medieval Manhattan," is famous for its soaring stone towers that rise dramatically above the Tuscan countryside. During the Middle Ages, wealthy families built these towers as symbols of power and prestige, and while only 14 of the original 70 remain, they still create a skyline unlike any other. Beyond its towering skyline, San Gimignano boasts charming medieval squares, frescoed churches, and a vibrant cultural scene. The Piazza della Cisterna, the town’s bustling heart, is lined with historic palaces, artisan shops, and wine bars serving the famous Vernaccia di San Gimignano, a crisp white wine unique to the region. The Collegiata di Santa Maria Assunta, with its stunning frescoes depicting biblical stories, is a must-visit for art lovers, while the walk along the medieval walls offers some of the best panoramic views of the Tuscan landscape. Whether you’re climbing a medieval tower, sampling world-class wine, or simply strolling through ancient alleyways, San Gimignano is one of the most captivating medieval towns in Italy.