David & Jayne
A Journey Through Southern Italy
This September, you’ll trace a path through some of Italy’s most storied landscapes — from the sun-drenched Baroque streets of Lecce to the cliffside charm of Monopoli, the iconic trulli villages inland, and the timeless caves of Matera. Along the way, expect long lunches, boutique stays, quiet corners of beauty, and a plan that encourages you to slow down and take it all in.
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This journey has been carefully designed to balance exploration and ease with space to indulge, pause, and connect with the richness of the south.
From family-run trattorias to Michelin-starred surprises, secluded masserias to rooftop aperitivo, every moment has been considered.
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Here’s what awaits.
Luxury Trip Plan
September 9th:
Arrival & Settle
Arrive in Puglia, pick up your hire care and head to Lecce, then check into the elegant Villa Acqua, your serene private home for the first part of the journey. Unpack, unwind, and enjoy your first evening at leisure—perhaps a glass of local wine by your private rooftop pool.
September 10th:
Baroque Beauty & Rooftop Cocktails
Spend the day exploring Lecce, the Baroque jewel of the south. Visit its iconic churches, stroll through golden-stone streets, and admire the architecture at every turn.
In the early evening, enjoy sunset cocktails on the rooftop at Patria Palace, followed by a relaxed dinner at your choice of local restaurants known for regional favourites and an elegant but unfussy atmosphere.
September 11th
Coastal Day Trip: Otranto & Salve
September 12th:
Pasta Making & Fine Dining in Lecce
Begin the day with a private pasta-making class, learning the techniques and traditions of southern Italy in an intimate kitchen setting. From shaping orecchiette to perfecting the simplicity of local sauces, it’s a hands-on way to engage with the region’s culinary heritage.
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Later, check into Pollicastro Boutique Hotel, one of Lecce’s most beautiful historic stays. You’ll be in the premier suite – the best room in the house, complete with its own private cave pool tucked beneath the original stone structure. It’s the kind of room you remember long after the trip is over — peaceful, dramatic, and deeply rooted in the building’s past, right in the heart of Lecce.
That evening, enjoy an unforgettable tasting menu at Michelin-starred Bros’, one of Puglia’s most avant-garde dining experiences.
September 13th:
Head North to Monopoli
Travel north toward the Adriatic and check into Aqva Luxury Suites in Monopoli, a design-forward boutique stay overlooking the sea.
Spend the afternoon exploring the town’s cultural side, including the Contemporary Art Museum or temporary exhibitions at local galleries. Dine locally in the evening—recommendations can be provided.
September 14th:
Alberobello & A Long Lunch at Il Cortiletto
In the morning, visit Alberobello, the UNESCO-listed trulli village. Wander its winding streets before heading to the countryside for a long, indulgent lunch at Il Cortiletto, known for refined interpretations of regional classics.
Return to Monopoli in time for sunset drinks and dinner on the rooftop at Don Ferrante, perched above the sea.
September 15th:
Slow Beach Day & Dinner in Fasano or Locorotondo
Take it slow with a relaxing beach day at one of Monopoli’s beach clubs—whether you prefer rustic or refined, we'll tailor this to your preference.
In the evening, head into either Fasano or Locorotondo for dinner at one of their quietly exceptional restaurants.
September 16th:
Head to Masseria Auraterrae
Move slightly inland and check into Masseria Auraterrae, a tranquil retreat surrounded by olive groves and sea views.
Just down the road, make your way to Terre di San Vito, one of the region’s most celebrated vineyards. Spend the afternoon on the estate with a wine tasting experience that many consider the best in Puglia. Alongside the estate’s elegant wines, you’ll enjoy a relaxed lunch among the vines — expect seasonal dishes, generous hospitality, and a true sense of place.
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Return to Auraterrae in the evening, where you can enjoy a quiet night in or take the hotel’s free shuttle down to Polignano a Mare for a stroll through town or dinner by the sea.
September 17th:
Reset & Rejuvenate
Spend the day making the most of Auraterrae. Whether it’s swimming, a spa treatment, or simply relaxing with a book and a view, today is about slowing down and soaking it all in.
September 18th:
Into Basilicata: Matera by Day & Night
Check out and head north into Basilicata, arriving in the ancient stone city of Matera—a cinematic marvel carved into rock.
Explore the town’s winding cave dwellings and historical sites before checking into Palazzotto Residence.
At sunset, sip cocktails at Zipa, then experience the magic of Matera lit by night with dinner in one of its hidden restaurants.
September 19:
The Final Stay, Ostuni
Return south for your final evening, checking into La Sommita Relais, a peaceful hideaway set within the old town of Ostuni.
Wander the labyrinth of whitewashed streets, pausing for sunset aperitivo at Borgo Antico, followed by dinner in one of Ostuni's candlelit cave restaurants.
September 20th:
Farewell Puglia
Spend the morning enjoying the hotel’s quiet comforts. Before your evening flight, take a final detour into Brindisi city for an early farewell dinner—one last plate of pasta, one last glass of local wine, before heading to the airport for your return to Manchester.
