From the UNESCO cave dwellings of Matera to a masseria in the Valle d’Itria, the Baroque streets of Lecce, and the Adriatic coast at Otranto, across nine days in the heel of Italy.
9 days
|From $7,000 pp
From the UNESCO cave dwellings of Matera to a masseria in the Valle d’Itria, the Baroque streets of Lecce, and the Adriatic coast at Otranto, across nine days in the heel of Italy.
This itinerary moves through the heel of Italy at a pace the region rewards. It begins in Matera, a UNESCO-listed city in Basilicata with cave dwellings carved into limestone cliffs across several thousand years of continuous occupation. From there the journey moves north into the Valle d’Itria, the rolling plateau of trulli houses and hill towns at the geographic center of Puglia, before heading south through Lecce and out to the Adriatic coast at Otranto.
Each section of the journey is distinct in character. Matera is ancient and specific, a city that looks, in the early morning before the tour buses arrive, almost exactly as it did when the families living in the cave dwellings were relocated in the 1950s. The Valle d’Itria is pastoral and slower, built around masserie, trulli, and the food culture of the Apulian countryside. Lecce is a city of Baroque architecture in local stone. Otranto is the point where the Adriatic and Ionian seas meet at the most easterly tip of Italy.
Do Not Disturb designs the full nine days around what each area produces at its best and how the journey moves between them.
Arrival into Bari Airport, followed by a private transfer south and east into Basilicata, approximately one hour by road. Matera sits on the edge of a ravine carved by the Gravina River, with the Sassi, the cave-dwelling districts of Sasso Caveoso and Sasso Barisano, spread across the gorge walls on both sides and the cathedral sitting on the highest ridge between them.
Your base for two nights sits within the Sassi themselves, placing you at the center of the cave-dwelling districts rather than on the plateau above. A private guide covers both districts on the morning of Day 2, including the cathedral, the rock-carved churches, and the history of the 1950s relocation program, in the first hour after the city opens before the group tours arrive from Bari. The afternoon is unstructured, suited to following the lanes of the Sasso Caveoso on foot.
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 south from the Valle d’Itria to Lecce, approximately one hour by road. Lecce holds a concentration of Baroque architecture in lecce stone, a local limestone that allowed the level of decorative detail covering the Basilica di Santa Croce, the cathedral, and the Palazzo dei Celestini. A private guide covers the cathedral, the Basilica di Santa Croce, and the Roman amphitheater in the morning, with the afternoon left for independent movement through the historic center.
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
A private transfer to Brindisi Airport, approximately one hour from Lecce, for onward flights. Bari Airport, around two hours from Otranto, provides an alternative. The itinerary can be extended with additional nights in Lecce, a side trip to Gallipoli, or a connection north to the Gargano peninsula.
A private walking tour of Michelangelo's Florence, from the David at the Accademia through the Medici Chapels, Casa Buonarroti, and Santa Croce. Arranged by Do Not Disturb.
A private sunset dinner on Lake Garda aboard a restored wooden boat, with lake fish and regional wines as the light drops behind the Alps. Arranged by Do Not Disturb.
A private truffle hunt in the Crete Senesi follows a local hunter and trained dog through Tuscany’s pale clay hills in search of seasonal truffles. The walk ends with a relaxed lunch built around what was found, turning one of the region’s oldest rural traditions into a personal, unhurried experience.
A full day on Lake Como by private wooden boat, from Bellagio to Varenna and along the western shore, with a captain who knows the villas and their histories. Arranged by Do Not Disturb.
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