Begin in Bari’s historic center, a maze of alleys, courtyards, historic buildings, and local life that feels like a city within a city. As you explore, take in its about 30 churches and notable architecture, including the Basilica of San Nicola, the Romanesque Basilica of San Gregorio, the Cathedral of San Sabino, and the Norman-Swabian Castle, commissioned by Frederick II.

Continue to Bari Vecchia, the ancient heart of the city on the largest waterfront in Italy. Move through streets shaped by the scent of laundry, freshly baked focaccia, and fresh pasta drying in front of doors, especially along Arco Basso and between Piazza Ferrarese, Piazza San Pietro, and the Monastery of Santa Scolastica. Also visit Piazza Mercantile, the infamous Column, and the Library of Santa Teresa dei Maschi.

Bari Vecchia is described as the ancient heart of Bari.

Take the train to reach today’s destinations. Tickets are not included. Start in the medieval village of Polignano a Mare, perched on a high, jagged coast and known for its alleys, white houses, and sea-facing loggias. Walk the elegant promenade, where the statue of the writer of the famous song “Volare” stands near the old city. Do not miss the “Pino Pascali” Museum Foundation, set in the former Municipal Slaughterhouse, with exhibitions, seminars, art events, and the “Pino Pascali” Award.

Continue with a boat tour from Polignano, lasting about 1 hour 30 minutes, with a 90-minute visit to the Polignano caves by boat. The tour starts from San Vito, a few kilometers north of Polignano, and includes time to swim, relax, and enjoy the panorama. Admire Polignano from the sea, its cliff, the grotta delle rondinelle, grotta Palazzese, grotta Ardito, grotta del Macello, many other caves, and the hermit’s rock. Then visit Monopoli, with its Adriatic setting, historic center, Porta Vecchia, city walls, Castle, noble palaces, religious buildings, and the baroque Cathedral of Santa Maria della Madia.

Polignano a Mare is described in this itinerary as a town perched entirely on the sea, with cliffs and many caves shaping its coastal landscape.

Pick up your rental car and begin the road trip portion of your journey.

Travel between Trani, Andria, and Bari, with the day centered on Castel del Monte. Described as a place of mysteries and magic, this XIII-century building was built by Emperor Federico II and is one of Puglia’s major symbolic sites. Its perfect geometrical design recalls an intricate labyrinth, where three imprints left by Federico II can still be found.

Castel del Monte is presented in the itinerary as one of the major symbolic places of Puglia.

Start at the Caves of Castellana, located about 40 kilometers from Bari and considered the most important speleological complex in Italy and Europe. Formed by the erosive action of an ancient underground river, the caves reveal limestone rock shaped over time into natural tunnels that wind through two paths.

Your entrance fee is included for the complete guided visit of the Grotte di Castellana. Continue to Alberobello, the city of Trulli, known for its unusual white houses with conical roofs. Discover Aia Piccola, one of the neighborhoods where people still live in a Trullo, before continuing to Martina Franca.

The cavity of the Caves of Castellana was discovered in 1938.

Travel to Matera, described as one of the oldest cities in the world. Its territory holds evidence of human settlement from the Paleolithic onward, without interruption until today, making it an extraordinary page written by people through millennia of long history.

Join a private guided tour of the Sassi district of Matera, lasting about 2 hours. The Sassi, meaning “pebbles,” are divided into Sasso Caveoso and Sasso Barisano, where houses are partly carved into limestone walls above the Gravina torrent. In 1993, the Sassi of Matera were listed as a World Heritage of Humanity as “the most remarkable and complete example of a set of cave dwellings in the Mediterranean region,” suited to its terrain and ecosystem.

The first inhabited area of the Sassi dates back to the Paleolithic.

Visit Ostuni, known as the White City for the characteristic color of its houses. Its historic center, called “La Terra” by local inhabitants, was once completely painted with white lime, which is now only partially preserved. The houses climb the steep sides of a hill, and the village is shaped by winding streets, small squares, alleys, and courtyards.

Continue through the coastal dunes park of Ostuni, a landscape of beaches, dolmens, karst blades, and ponds populated by herons and egrets. The Regional Natural Park “Coastal Dunes from Torre Canne to Torre San Leonardo” extends over Ostuni and Fasano, running through kilometers of beaches toward the olive-tree plain. Excursions and guided tours start at the former Fontevecchia station, now the Park House, and the ancient Via Traiana leads to the Montalbano dolmen, dating to around the second millennium BC.

Ostuni’s historic center is called “La Terra” by its inhabitants.

Spend the day in Lecce, known for its artistic and cultural heritage. Walking through its streets, you encounter the warm, enveloping tones of Lecce stone and ancient buildings that shape the city’s character. The day’s setting ranges from its oldest monuments and most famous squares to its beaches and more intimate, hidden corners.

Join the HD Lecce Cooking Class, Pasta making with Matilde, at her home in Lecce. She teaches you how to make Pugliese pasta, starting with dough made from flour and water, then shaping it into forms such as typical orecchiette. After preparing the pasta, enjoy an antipasto with local products such as cheeses and taralli while it cooks, then taste it with local sauce. During the meal, Matilde shares her passion for cooking and Apulia. Some other members of her family might join you.

Lecce stone is specifically noted in the itinerary for giving the city’s streets their warm and enveloping tones.

Visit the ancient village of Gallipoli, perched on its characteristic islet. Begin by following the road clockwise from the ramparts, where the route first meets the Church of San Francesco da Paola, noted for its simple facade. Continue to the Church of Santa Maria della Purità, the oldest church, seat of the homonymous brotherhood, and a precious art gallery.

The sacred buildings continue along the sea as you complete the circumnavigation of the village. Take via De Pace, the street that cuts the village in two, and arrive in front of the Cathedral of Sant’Agata. This cathedral is described as one of the greatest examples of Salento baroque and forms the main architectural focus of the old village route.

The Cathedral of Sant’Agata is identified in the itinerary as one of the greatest examples of Salento baroque.

Explore Otranto, where the day offers several possibilities. You can spend a few hours relaxing on one of the city’s two small beaches or go a few kilometers farther to reach some of Italy’s most beautiful beaches. The town also has numerous pubs, pizzerias, ice cream parlors, and small shops selling souvenirs, handicraft, and traditional productions, open during the day and often until late at night. Continue toward Roca Vecchia, Grotta della Poesia, and Torre dell’Orso.

Visit Torre Sant’Andrea, an ancient fishing village a few kilometers north of Otranto, near Melendugno. Along the Adriatic coast of Salento, between Baia dei Turchi and Torre dell’Orso, see the Sea Stacks of Torre Sant’Andrea, limestone formations shaped by water and reflected in clear sea. This rocky seaside area has small coves, a beach framed by a sixteenth-century defense tower, a small harbor, and white rock guardians. The “Arco degli Innamorati” has an arch shape that can be crossed by swimming. Behind the jagged coast, ravines, and caves, a pine forest offers shade, picnic space, green paths, and rock-cut ladders leading to small sandy coves when the tide is low and the sea is calm.

Torre Sant’Andrea has received the Blue Flag and the 5 Sails of Legambiente several times.

Begin your departure day in San Cesario di Lecce. This final day is focused on closing the road trip portion of your journey and preparing to leave after traveling through Puglia by rental car.

Turn in the rented car to the rental office nearer to you. Keep the timing and location aligned with your onward plans, while preserving the itinerary’s instruction to return the vehicle at the rental office nearer to you.

San Cesario di Lecce is the departure point listed for the final day of the trip.