Luxury Puglia Tour: Matera, Lecce and Otranto

A private transfer north and west from Matera crosses back into Puglia and onto the Murge plateau, descending into the Valle d’Itria. The landscape changes within the first hour, the gorge walls of Matera giving way to a rolling plateau of olive trees and dry stone walls. Your base for three nights is a masseria within the Valle d’Itria, selected for its position within the landscape and its direct connection to the food culture of the Apulian countryside, with breakfast and dinner drawing on what the farm and surrounding area produce.

Alberobello, the UNESCO-listed town of trulli houses, is 20 minutes from most masserie in the central valley. A private guide covers both historic neighborhoods in the early morning before the tourist groups arrive, covering the construction method and the specific history of the trulli as a tax-avoidance strategy under the feudal Kingdom of Naples.

A private driver connects Locorotondo, Cisternino, and Martina Franca on the second day, with lunch in Cisternino known for its bombette, rolled pork parcels cooked over open coals specific to this part of Puglia. Ostuni, on the eastern edge of the valley looking toward the Adriatic, is 30 to 40 minutes from the masseria base and worth a morning before 10am.

A private transfer east from Lecce to Otranto, approximately 45 minutes by road. Otranto is the most easterly town in Italy, its old town enclosed within medieval walls above a harbor in continuous use since the Greek and Roman periods. The cathedral holds the Pantaleone mosaic, a floor covering the full nave in a Tree of Life composition with figures from the Bible, mythology, and medieval history, completed between 1163 and 1165.

The chapel of the Martyrs holds the remains of the 800 citizens killed by Ottoman forces in 1480, and the Aragonese Castle on the harbor operates as a museum and exhibition space. The Cava di Bauxite, an abandoned quarry two kilometers from the center, holds a lake surrounded by red earth walls reached by a 20-minute walk, with the path back to Otranto passing Baia dei Turchi, one of the most secluded beaches on the Adriatic coast.

On the second day, a private driver follows the SP358 coastal road south from Otranto toward Santa Maria di Leuca, 60 kilometers of cliffs, fishing harbors, and swimming coves, with stops at Castro, Santa Cesarea Terme, and Tricase Porto at the guest’s own pace. Santa Maria di Leuca sits at the tip of the Italian boot where the Adriatic and Ionian seas meet