After a relaxed start in Matera, drive southeast and plan a mid-morning arrival in Alberobello to wander the UNESCO-listed trulli district; stop at a local craft shop to see how the cone roofs are restored and grab espresso at Rione Monti while admiring the stonework. Continue with a short, scenic drive to the countryside outside town for a tasting at Cantina or an olive oil frantoio where you can sample freshly pressed oil and buy a bottle to enjoy later in Ostuni.
After your Alberobello morning, drive on to Ostuni and check into your accommodation before heading out to explore the lower town; stroll the sunlit lanes toward Piazza della Libertà and pause for a late lunch or aperitivo on the terrace of Corte di Ostuni to watch locals meander by. Continue with a relaxed wander to Porta Napoli and the panoramic Belvedere Santa Lucia, where you can photograph the whitewashed houses spilling down to the olive-grove countryside, then finish the afternoon with a visit to Museo Civico for local history and artifacts before an early evening gelato.
As twilight deepens, wander the winding lanes up to Piazza Cattedrale to catch the golden glow on the whitewashed facades, then settle in for dinner at Osteria del Tempo Perso, where regional specialties like orecchiette with turnip tops and local Nero di Troia red are served in a cozy, vaulted dining room. Afterward, enjoy a relaxed passeggiata to Belvedere Sant'Oronzo for a night view over the illuminated town and finish with a digestivo or espresso at Bar Centrale, perfect for soaking up the evening atmosphere before turning in.
Start your day with a sunrise coffee at Piazza della Libertà then head to the quieter lanes toward Chiesa di San Vito to admire Baroque details before the crowds arrive. From there, join a guided walking tour that climbs to Belvedere Sant'Oronzo for sweeping views of the countryside and stops at a traditional bakery on Via Cattedrale to sample warm focaccia barese and freshly squeezed orange juice.
After a morning spent in the heart of Ostuni, head down to the waterfront fringe for a leisurely lunch at La Taverna della Papessa where seafood mezzes and a local rosato pair perfectly with sea breezes; afterwards, stroll the shady lanes to Parco Duna Costiera for a peaceful walk among Mediterranean scrub and panoramic views of the Adriatic. Finish the afternoon with a visit to Museo della Civiltà Contadina to learn about rural life in Puglia and stop at Antica Salumeria to pick up local cheeses and cured meats for a picnic as the light softens toward evening.
As the sun softens, follow cobbled lanes upward to Piazza Cattedrale Vecchia to watch golden light wash the cathedral steps, then slip into Antica Osteria di Porta Nova for a tasting menu focused on local capocollo and slow-cooked lamb paired with a crisp Verdeca. After dinner, take a short stroll to Terrazza del Carmine for panoramic night views of the olive-studded valley and finish with a nightcap at Enoteca del Borgo, sampling regional grappas while listening to the town settle into evening calm.
Leave Ostuni early for a refreshing seaside morning at Riserva Naturale di Torre Guaceto, walking the dunes and snorkeling in the protected coves before enjoying a beachside breakfast at La Spiaggia del Gelsomina where you can taste freshly caught fish and granita. Alternatively, drive inland to the baroque lanes of Martina Franca to join a local food tour that visits Mercato Coperto for burrata tastings and pastry stops at Pasticceria Le Delizie, then climb to the panoramic terrace of Palazzo Ducale for views over the Valle d'Itria.
Drive from Ostuni toward the coastal town of Villanova for a relaxed seafood lunch at Ristorante Da Filippo, then rent bikes nearby to pedal the salt-pan trails of Riserva Salina di Fogliano, spotting wading birds and salt-harvesting terraces. Later, detour inland to the hilltop hamlet of Ceglie Messapica to wander its stone streets, visit Museo Civico Archeologico for regional finds, and enjoy a late-afternoon tasting of local olive oils and artisanal breads at Frantoio Ridolfi before returning to Ostuni as the light softens.
After a day of sea or valley exploration, drive back toward Ostuni and pause at Torre Pozzelle for a tranquil sunset walk along the limestone cliffs and salt-tinted pools, where local fishermen mend nets and the light turns warm. Return to town for a relaxed dinner at Borgo Antico Ristorante, savoring seafood crudi and a glass of local primitivo, then end your evening with live music and cocktails on the terrace of Caffè Sgubbi, watching the whitewashed rooftops glow under the stars.