Spend your first day exploring Puglia's vibrant port city of Bari. In the morning, take a walking tour of Bari's medieval old town to see historic sights like the 11th century Basilica di San Nicola, overlooking the harbor. Then visit the ornate Bari Cathedral, seat of the local archbishop. For lunch, indulge in fresh seafood at Michelin-starred Il Pescatore restaurant.
In the afternoon, wander through Bari's Murattiano neighborhood to window shop local designers and explore the Archaeological Museum. Cap off the day with dinner at intimate Gastronomia D'asino, savoring antipasti and handmade pastas near the citadel walls. Retire to luxury accommodations at the Excelsior Bari Palace, overlooking the Adriatic Sea.
On your second day, head inland to Alberobello. Wander past the magical circular stone trulli huts of the Rione Monti district and take pictures next to the two-story Trullo Sovrano with its distinctive spire. Stop for lunch at Trattoria Terra Madre to feast on Puglian specialities like orecchiette pasta and bombette meat rolls with views of the trulli rooftops.
Then continue on to the beautiful whitewashed hilltop town of Ostuni. Stroll the winding white alleys and marvel at Ostuni's olive groves from Piazza della Libertà. End the day with an atmospheric dinner of octopus salad and fresh seafood at Osteria del Tempo Perso, set inside a candlelit cave. Stay overnight at Trulli Holiday Resort, amidst modernized trulli stone cottage accommodations.
On your third day explore Lecce, known as the "Florence of the South" for its ornate Baroque architecture. In the morning, take a guided walking tour of Lecce's beautiful churches and piazzas, including the 12th century Basilica di Santa Croce and the bustling Piazza del Duomo anchored by a Roman amphitheatre. Stop for a long lunch at Le Zie to dine on pastas paired with local Primitivo wine.
In the afternoon, visit papier-mâché studios to learn about Lecce's artisanship and the 16th century underground archaeology museum Museo Faggiano. End your day at upscale restaurant U'Ncuc savoring creative local cuisine. Retire to the boutique hotel Casa dei Mercanti nestled in Lecce's historic center.
On day four, head south along the coast to the charming cliffside town of Polignano a Mare. Spend the morning relaxing on the sunny sands of Lama Monachile Beach and browsing the seaside shops and boutiques in town. For lunch, walk to Friggitoria Masseria Calderisi to enjoy casual fried seafood like anchovies and cod croquettes.
In the afternoon, take a boat tour to better admire Polignano's dramatic sea caves and limestone cliffs towering above the azure waters. After swimming, enjoy an indulgent seafood dinner at Grotta Palazzese, set inside a cliffside cave perfectly framing the sea. Stay the night at the same luxury hotel, Grotta Palazzese.
On your last day, journey to the ancient cave city of Matera, a 2019 European Capital of Culture. In the morning, join a guided tour of Matera's sassi cave district to explore the stone carved churches, rock-cut houses, and winding alleys. For lunch, stop at cozy bistro Area 8 for modern Puglian cuisine.
Spend the afternoon seeing top sites like the Cathedral of Sassi, the primitive cave dwelling Casa Grotta di Vico Solitario, and the contemporary art museum MUSMA. Enjoy a memorable farewell dinner at acclaimed Casa Grotta restauraasting traditional Basilicata dishes. Stay the night at Locanda di San Martino, an elegant hotel set inside ancient caves.