Otranto

Leave the castle through the small Porta Alfonsina, climb the narrow stepped lane of Via Basiliani for four minutes through whitewashed houses, and the unassuming Romanesque facade appears almost without warning. Inside lies the reason every traveler in Salento eventually comes to Otranto: 16,000 square feet of 12th-century mosaic floor — the Tree of Life by the monk Pantaleone — covering the entire nave like a frozen tapestry. Walk the wooden planks slowly; this is one of the largest medieval mosaics in Europe and it is entirely free.

Tip: Step into the right transept to find the Chapel of the Martyrs — the glass cases hold the actual skulls of the 813 citizens beheaded by the Ottomans in 1480. Most tour groups miss it because it is unmarked on the floor plan; arrive before 10:30 and you will have it to yourself.

Exit the cathedral, turn right onto Via Duca degli Abruzzi and follow it east for six minutes until the alleys spill abruptly onto the city walls. The Pelasgian Bastion is the north-east corner of the old town — a flat stone terrace dropping straight into water so clear you can see the rocks twenty feet down. This is the first place on the route where you face directly toward Albania; on a clear morning you can pick out the Karaburun peninsula on the horizon, 80 km away.

Tip: The flat stone slabs to the left of the bastion are where locals jump in for a swim — if you brought swimwear under your clothes, this is your one chance today, and the water is calmer here than at any beach because the bastion blocks the swell.

Walk back into the old town along Corso Garibaldi for four minutes — the Salento sun is now overhead and the lane smells of almond. Martinucci is the Salentine pastry institution, and their Otranto counter does the regional specialty fast: a puccia (a soft round bread split open and stuffed) with capocollo, mozzarella and grilled vegetables for around €7, and a pasticciotto leccese — warm shortcrust filled with custard — for €1.80. Eat standing at the counter; this is exactly how locals do lunch in summer.

Tip: Order the pasticciotto al pistacchio, not the classic one — the pistachio version is what residents from Lecce drive down specifically for. Ask for it 'caldo' (warm) and they will pull one from the oven tray; never accept a refrigerated pasticciotto, the custard turns gummy.

From the pastry shop, walk south along the Lungomare degli Eroi past the small Byzantine church of San Pietro, follow the coastal road as it curves past Baia dell'Orte, then pick up the cliff trail at Torre del Serpe — about 5 km one-way along bare limestone cliffs the color of bone, with the Adriatic 50 m below. Punta Palascia is the easternmost point of Italy; the small black-and-white lighthouse marks the exact line where the Adriatic ends and the Ionian begins, and on a clear afternoon you genuinely see the two seas meet in a long ripple. You came to Otranto to say you'd been; this is the photograph that proves it.

Tip: Wear real shoes, not sandals — the trail is sharp karst rock and there is zero shade for the full distance. Carry 1.5L of water from town; the only fountain on the route is at Torre del Serpe and it is sometimes dry in August. Turn back by 17:30 or you will be walking the cliff edge in fading light.

Walk back into the old town through Porta Terra — eight minutes from the harbor along Via Cenobio Basiliano. After 15 km on your legs you have earned a proper sit-down, and L'Altro Baffo is where chef Christian Cosi reinterprets Salento seafood with the restraint of a fine-dining kitchen. Order the raw red prawns of Gallipoli (€22) — sweeter than any langoustine you have eaten — and the spaghetto with sea urchin and lemon zest (€26). The wine list leans hard on Salentine Negroamaro; ask the sommelier for a glass of Calafuria rosé from Tormaresca.

Tip: Reserve before 18:00 the same day or you will not get a table — the dining room is small and books out from June onward. Avoid the restaurants on Lungomare degli Eroi with the printed photo menus and English-only barkers; they are the classic Salento tourist trap, charging €30 for frozen fritto misto that costs €12 inland.

Exit the cathedral, turn left into Via Duca degli Abruzzi, and walk five minutes through whitewashed alleys hung with laundry and bougainvillea to reach this tiny 10th-century Byzantine church. Built on a Greek cross plan, it still holds faded frescoes of the Last Supper on its central dome; fifteen minutes inside is enough. Afterwards, lose yourself in the labyrinth around Via Pretoria and Via Cattedrale — every wall lime-washed white, every door Greek-island blue, every corner a photograph.

Tip: San Pietro closes at 12:00 for the long lunch break and does not reopen until 16:00 — be inside by 11:45 at the latest. The dome frescoes are clearest standing directly under the centre looking up at a 45-degree angle; flash is forbidden but a steady phone at 1/15s works.

Two minutes from San Pietro on Via Rondachi — a noisy family trattoria where the lunch crowd is fishermen, masons, and off-duty carabinieri from the station up the road. Order the puccia salentina al tonno e capperi (€8, a round flatbread split open and stuffed with tuna, capers, and Pachino tomato) and a half-portion of orecchiette con cime di rapa (€9). A glass of Negroamaro is €4 — this is what locals eat on a Tuesday.

Tip: Arrive by 12:30 or expect a 20-minute wait — they do not take lunch reservations. Skip dessert here and walk five minutes back to Pasticceria Martinucci on Corso Garibaldi for a pasticciotto leccese (€1.80), the warm custard tart Salentini have for elevenses.

Walk south down Corso Garibaldi for three minutes — the castle's pentagonal bulk grows out of the harbour cliffs ahead. Built in 1485 on Ferdinand of Aragon's orders to harden the town against another Ottoman raid, this fortress so haunted English diplomat Horace Walpole that in 1764 he wrote the first Gothic novel and named it The Castle of Otranto. Walk the ramparts first, then descend into the dry moat and dungeons; the upper rooms host rotating contemporary-art shows.

Tip: Go straight to the eastern seaward rampart first — by 16:00 it fills with cruise-ship day-trippers bussed in from Brindisi. From that bastion the view stretches all the way south to Punta Palascìa, a useful preview of tomorrow's walk.

Exit the castle by the western gate, drop down to the Lungomare degli Eroi, and walk twenty minutes north along the seafront — the curve of the bay opens up with the cathedral campanile floating above the white roofs. At the far end, climb up onto Porta Alfonsina (the 1481 town gate rebuilt after the Ottoman siege), then on into the Bastione dei Pelasgi: cyclopean stones believed to predate Greek Otranto by a thousand years. The setting sun is behind the town, so the white facades burn honey gold from the west while the Adriatic behind you darkens to ink.

Tip: Position yourself on top of Porta Alfonsina at 18:30 facing east — at exactly that hour the cathedral campanile catches the last warm light against a deep blue dusk sky. The benches along the inland side of the bastion are the only ones in town that face the actual sunset; everyone else is staring at the sea in the wrong direction.

Five minutes back through the old town on Via Cenobio Basiliano — a small modern dining room with eight tables, run by chef Cristina Conte who refined her family trattoria into Salento's most quietly exciting kitchen. Order the crudo di gambero rosso di Gallipoli (€22, raw red prawns from the Ionian, dressed with citrus and Salina capers) and the spaghetto ai ricci di mare (€26, with sea urchin pulled that morning). Pair with a Susumaniello rosato from Brindisi (€8 a glass); the seven-course dégustation is €70.

Tip: Reserve at least three days ahead in summer, a week in August — booking via Instagram DM gets faster replies than the phone. Pitfall warning: most of the lungomare restaurants with photo menus and English-speaking touts at the door are tourist traps charging €30 for frozen calamari; the rule is simple — no chalkboard menu in Italian, no real meal.