Gallipoli sits on the Ionian coast of Salento, in the heel of Italy’s boot. Its name comes from the Greek Kallipolis, “beautiful city,” and the first glimpse of the old town on its small limestone island explains why. Walls rise straight out of turquoise water, fishing boats rock in the harbor, and a stone bridge connects it all to the mainland. Most visitors arrive for the beaches and leave without understanding the town. This guide shows how to see the old town, the coast, and the living culture in one well-paced day. Crossing the Bridge to the Island The old town begins at the 16th-century bridge, which for generations was the only way on or off the island. Once across, the noise of the modern town fades. The lanes are narrow, whitewashed, and bent on purpose, a design that kept out both sea winds and unwelcome visitors. Start early. Between 8 and 10 in the morning, the light on the stone is soft, shopkeepers are still opening shutters, and you can walk without dodging crowds. Wear ...