A four-day tour in the footsteps of the Messapians, the ancient people of the heel of Italy: the port of Brindisi, the megalithic walls of Manduria, Muro Leccese and Vaste, the clifftop town of Castro and white Ostuni. It starts and ends in Brindisi.
In antiquity, the south of Puglia belonged to the Messapians, an ancient people whose walls, tombs and old roads still turn up all over the Salento, the peninsula at the very tip of the region. This tour starts from their port, Brindisi, and follows their traces from site to site, with archaeology, wine, the sea and whitewashed hill towns along the way.

Day 1: Brindisi and its historic port
The journey begins in Brindisi, a city with deep Messapian roots. A guided tour takes you to its harbour, overlooked by the terminal columns of the Via Appia, the great Roman road that ended here, and by the Monument to the Sailor. After lunch in town the afternoon is free, to explore further or simply to rest. Back to the hotel for dinner and the night.
Day 2: Manduria, wine and ancient walls
The day starts in Manduria, a town known for its wines and above all for Primitivo di Manduria, the red that carries its name (more in our guide to Primitivo and Negroamaro). The place also has a very old history: Pliny may have described it through its mysterious Fonte Pliniano, a natural cave with a steady supply of lightly mineral water. The site holds many Messapian remains: a ring of megalithic walls, built from huge blocks of stone, ancient burials and the traces of old roads.
In the afternoon the tour moves on to Cavallino, near Lecce, to visit its museo diffuso, a “spread-out museum”: an archaeological area you walk through with a guide rather than a building with display cases. Back to the hotel for dinner and the night.
Day 3: Muro Leccese, Vaste and Castro
After breakfast, the tour heads to Muro Leccese, a village that goes back to the Middle Ages and still keeps many Messapian traces, from fortifications to tombs. A short drive away, the archaeological area of Vaste is what remains of an ancient Messapian city in the heart of the Salento.
Lunch is at a restaurant by the sea, followed by a visit to Castro, a small town perched on the cliffs, which the Messapians used as a lookout facing east, towards the lands across the sea. Back to the hotel for dinner and the night.
Day 4: Ostuni, the white town
The last day takes you to Ostuni, an old town with a Messapian name, built across three hills. Here you see the 15th-century cathedral and the old town, with its houses painted white with lime. Lunch is in town, and the afternoon is free for browsing the shops and for a sweet made with almond paste, with a Salento-style coffee on the side. Return to Brindisi, where the tour ends.
More tours. This route is one of our multi-day itineraries in Puglia, from the Gargano down to the Salento. For shorter routes and ideas by area, see all our itineraries in Puglia.






