Alison & Jonnie
A Journey Through Southern Italy
This week-long itinerary takes you through some of the most characterful corners of southern Italy, from the historic streets of Lecce to the relaxed coastline of Monopoli, finishing in the striking cave city of Matera.
Each stop has been chosen for its balance of atmosphere, comfort, and simplicity. Expect good food, well-designed stays, and plenty of time to explore at your own pace.
Nothing rushed, nothing overdone just a considered route through one of the most quietly beautiful regions in Europe.
Luxury Trip Plan
June 14th:
Arrival & Welcome to Lecce
Arrive at Brindisi Airport, where your Fiat 500 (or similar) will be waiting. From here, take a scenic drive to Palazzo Console in Lecce, the baroque capital of the south.
Hotel Address: Via Colonnello Archimede Costadura, 47, 73100 Lecce LE
Parking: Paid on street parking outside the hotel. Hotel staff will advise on long term parking the next day.
Check in to your Queen Superior Room, your home for the next three nights — a refined and peaceful base within walking distance of Lecce’s golden-stone streets, churches and bars.
June 15th:
Explore Lecce & Surroundings
Enjoy a full day in Lecce at your own pace. Take in the city’s architectural landmarks, independent boutiques, and shady piazzas. In the early evening, head up to the rooftop at Patria Palace for a cocktail with a view, followed by a relaxed local dinner nearby.
June 16th:
Coastal Drive or Stay Local
Today is yours to enjoy. You can stay in Lecce, dipping in and out of galleries and slow lunches, or take a short train ride to Ostuni and enjoy a boozy lunch. Alternatively visit Ostuni tomorrow by car.
Return to Lecce for your final night in the city.
June 17th:
Ostuni & Monopoli
Check out and begin your drive north to Monopoli. On the way, stop for lunch in Ostuni, (if you didnt visit yesterday) the famous white city, known for its winding streets and panoramic views.
Continue on to Monopoli and check into your Superior Sea View Room at Molo Suites.
Address: Largo Fontanelle, 15, 70043 Monopoli BA
Spend the afternoon exploring the town’s harbour and exhibitions. Dine locally.
June 18th:
Trulli Towns & Long Lunch
Head out early in your car for a day trip to Alberobello and Locorotondo, two postcard-perfect towns known for their conical trulli and whitewashed facades.
On the return journey, stop for lunch at Il Cortiletto, one of the region’s most hidden countryside restaurants. Return to Monopoli for a low-key dinner.
Restaurant Address: V. Lecce, 91, 72015 Speziale BR
Look for the restaurant pictured below:
June 19th:
Wine Tasting & Polignano by Night
Take a short train ride from Monopoli to Polignano a Mare & pick up a TukTuk either directly outside the station or over the bridge in the main town where they will take you to a wine tasting and late lunch experience at the esteemed Terre Di San Vito. Nestled in the heart of the Puglian countryside, this idyllic vineyard promises an unforgettable culinary journey. Your reservation is at 10:30am so please leave plenty of time to get there to avoid missing your slot.
Address: Tenuta Terre di San Vito, contrada Rascinuso, 70044 Polignano a Mare BA
You will need cash for the TukTuk (around 20 Euros each way) & your wine tasting experience can be paid directly at the vineyard (cash or card 100 Euros per person).
Spend the afternoon exploring Polignano a Mare. We recommend staying for dinner before taking the train back to your accommodation in Monopoli.
June 20th:
Monopoli to Matera
Check out and drive inland to Matera, the ancient cave city of Basilicata.
Check in to Moyseion, an intertactive boutique hotel carved into the rock, and explore the city’s unique stone paths and architecture.
Address: Gradelle S. Nicola del Sole, 3, 75100 Matera MT
Use your satnav or google for parking in Matera.
In the evening, enjoy cocktails at Zipa Café followed by dinner in the heart of the Sassi.
June 21st:
Farewell Puglia
Return your rental car in the morning. If time allows 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.
