Seven nights from the cave dwellings of Matera to the Baroque heart of Lecce and the whitewashed masserie of the Adriatic coast

Puglia is Italy at its most generous: long tables, olive oil pressed down the road, and a coastline that still feels like a discovery. The trip moves in three acts. One night in Matera, where you sleep inside the ancient Sassi and dine by candlelight in an 11th-century cave church. Three nights in Lecce, the “Florence of the South,” with its honey-colored Baroque streets, a market morning, a cooking class, and a day under sail off Otranto. Then three nights at a fortified masseria near the sea, with e-bikes through the Itria Valley, burrata still warm from the farm, and a picnic beneath olive trees older than most cathedrals. Days are paced for every generation, with hands-on cooking, swimming stops and short rides, and the afternoons stay open for the pool. Every element here (pace, hotels, activities, length) is built to be adjusted around you.

Sextantio Le Grotte della Civita

La Fiermontina

A private driver meets you at Bari airport for the hour’s drive into Basilicata and Matera, one of the oldest continuously inhabited cities in the world. In the afternoon a local guide leads you through the Sassi, the cave neighborhoods carved into the ravine. That evening a private chef serves dinner inside an 11th-century cave church.

Grottaglie ceramics & masseria lunch

A private driver takes you east toward Lecce, with two stops on the way. The first is Grottaglie, where ceramic workshops have lined the same quarter for centuries, including a visit to a private ceramist’s home. The second is lunch at an organic masseria winery, where the owner and chef pair native grapes with dishes from their own land. Arrive in Lecce in the afternoon and settle into La Fiermontina.

Lecce, market to table

A morning walk with a local guide through the “Florence of the South”: Baroque basilicas, Roman ruins and the craftsmen still working in papier-mâché. Then meet your chef at the Porta Rudiae market to choose the day’s produce, and walk to her kitchen to cook a four-course meal of Salento recipes before sitting down together to eat it.

Sailing the Otranto coast

A day on the Adriatic aboard a private sailboat off Otranto, with limestone cliffs, sea caves and coves for swimming, plus local wine and small bites of Salento on board. Afterward, wander Otranto’s old town and climb the walls of its Aragonese castle before heading back to Lecce for an evening making pizza or pasta together, everyone with their hands in the dough.

Luminarie & the Adriatic coast

Leave Lecce for the Itria Valley coast, stopping on the way to meet the artisans behind the luminarie, the lit wooden archways that turn Puglia’s streets into cathedrals of light at every festival. Arrive at Masseria Torre Maizza in time for a long lunch and an afternoon by the pool.

E-bikes & burrata

A guided e-bike ride through the Itria Valley, past trulli, dry-stone walls and the white hill towns of Locorotondo and Cisternino, with a guide riding alongside and a support vehicle behind. The ride ends at a family dairy farm where you make burrata by hand and taste it straight from the bowl.

Ostuni & the olive groves

A morning in Ostuni, the “White City,” followed by a guided walk through the countryside of Alto Salento, among wildflowers and olive trees, some more than a thousand years old. Lunch is a picnic laid out in the grove. The afternoon is free at the masseria.

One last slow breakfast before a private transfer to Bari or Brindisi airport, or carry on to Sicily, or north to the Amalfi Coast.