A town of two halves jutting out into the Ionian Sea, Gallipoli straddles a sixteenth century stone bridge connecting an island to the mainland. In the labyrinth old quarter, elegant nineteenth and eighteenth century stone-paved streets are partially enclosed by medieval walls with views across to the incongruous glass skyscraper in the new town and a picturesque old stone gatehouse on a pier in the middle of the wide bay. At Gallipoli's heart, is the cathedral of Sant'Agata (from the seventeenth century), which has a graceful and incredibly-ornate Baroque façade. It is surrounded by fine old town houses with wrought iron balconies and period lamps. There are stalls selling tourist tat, but old Gallipoli also has plenty of real shops, plus some decent restaurants and coffee shops.
Tree-lined main drag
Guarding the entrance to the old town, is a low-lying Aragonese castle with circular stone walls, overlooking yachts with towering masts and creaking fishing boats. Across the bridge, lined with tourist stalls, is a handsome, heavily-weathered, fountain intricately-carved from the creamy limestone found in Puglia. Behind the fountain is an appealingly-broad promenade running along the waterfront. And even Gallipoli's new town has its charms – the tree-lined main drag is paved with elaborate patterns and there is a pleasant park opposite a striking, modern church. On a summer evening, Italians in their glad-rags stroll from restaurant to gelateria to coffee shop, enjoying Gallipoli's laid-back, seaside ambiance. 8/10