While Tuscany has several walled towns, the most famous "fully encircled" city is Lucca. Its Renaissance-era walls are 4.2 kilometers long and, uniquely, have remained completely intact and were never used for military defense. Today, the tops of the walls serve as a public park and elevated pedestrian path, where locals and tourists bike and jog under rows of plane and chestnut trees. Another highly famous "walled" destination is San Gimignano, known as the "Manhattan of the Middle Ages" for its 14 surviving medieval towers enclosed within a 13th-century wall. For fans of film and fantasy, the tiny hilltop village of Monteriggioni is also iconic, with its perfectly circular walls and 14 square towers mentioned in Dante's Divine Comedy. While Lucca is the largest "living" city within walls, these three together represent the pinnacle of Tuscan medieval and Renaissance urban preservation, offering a literal step back in time for anyone walking through their ancient stone gates in 2026.