Uncover Italy’s ancient south on an intimate journey where whitewashed villages, sunlit seas, and timeless traditions come to life. We’ll wander Lecce’s baroque streets, step into the cave homes of Matera, a UNESCO World Heritage site, and sail the turquoise Adriatic Sea to secret coves and stunning views. Enjoy quiet evenings in the white city of Ostuni after days filled with local discoveries. Along the way, meet artisans who preserve centuries-old crafts and taste the flavors of a land steeped in history.

Our days unfold slowly and richly: sampling olive oil pressed from thousand-year-old trees, sipping wine among limestone vineyards, and visiting local dairies to see cheese made the way it has been for generations. Evenings invite conversation and connection as we share stories over rustic southern meals and regional wines.

With boutique hotels, private guides, and seamless logistics, this tour invites you to experience Southern Italy’s raw beauty and living traditions. Scroll down to see the tour inclusions and a more detailed itinerary.

Upon your arrival in Rome, your transfer will bring you to a small, charming, four-star resort on the coast of the Tyrrhenian Sea, at the mouth of the river Tiber. You have a spacious private room, and we have a reservation for a group dinner at the hotel's charming restaurant that evening.

If time allows, we can visit Ostia Antica, an extraordinary Roman site near Fiumicino, home to the ruins of the ancient port town that served as the gateway to Rome. Tracing its roots back to at least the 4th century BC, Ostia Antica served as Rome’s principal port for hundreds of years: a witness and monument to the rise of the ancient superpower, its dominance, and eventual decline.

The next morning, after a delicious breakfast, we will make our way to Brindisi, where our driver will take us to our first stop...

The southern area of Puglia is known as Salento, and here you find the town of Lecce. Often called the Florence of the South, this walkable town is rich in history. Ranging from a Roman Amphitheater uncovered during the fascist era to stunning church facades crafted during the opulent 17th-century period of Baroque architecture. Honey-hued stone gives Lecce a soft glow, and the streets invite you to stroll and window shop.

A private transfer brings us into the city, where we’ll stay at a four-star hotel in the historic city center for the next two nights, with breakfast included each morning. Our central location makes it easy to explore the city and enjoy dinners at local trattorias. Lecce is meant to be savored, with layers of beauty at every turn—from charming shops to remarkable churches that make it a true visual feast.

During our time in Lecce, we will embark on a walking tour with Sarah, a local archaeologist and historian. She will share some of the city's history, from the Ancient Romans to the Mussolini-era fascists. We will visit artisan workshops, stop for a Caffè Leccese, and learn about the hidden messages on the exquisite facades of baroque churches.

Known as the White City for the pale local stone used throughout its historic center, Ostuni is a postcard-perfect hill town filled with cafés, boutiques, wine bars, and inviting restaurants. During our stay in Ostuni, we have a charming 8-bedroom private villa located in the heart of the old town, all to ourselves! You’ll enjoy a private room and private bathroom, with breakfast served each morning by our host.

During our time in this part of Puglia, we’ll take day trips to nearby villages to meet local artisans and discover traditions unique to the region, including the ceramic workshops of Grottaglie. We’ll visit small, local vineyards producing distinctive wines of the area, such as Primitivo di Manduria, and stop at a family-owned masseria for tastings of fresh regional cheeses and local olive oil. One afternoon, we’ll head to the coast for a private sunset sailing experience on the Adriatic, complete with a classic aperitivo and sweeping coastal views. With a private car and driver at our disposal, we’ll enjoy the flexibility to explore the lesser-known towns that make Puglia so special.

Each evening, we’ll return to Ostuni for aperitivo with views toward the sea, relaxed dinners, and a gentle passeggiata through the glowing white streets on our way back home.

A private transfer will take us to our final stop: Matera. Considered the oldest continuously inhabited settlement in Italy, many of its residents lived in cave dwellings until the 1950s. Dramatically set along the edge of a deep river gorge, this extraordinary city is layered with history, character, and quiet beauty. Its otherworldly landscape has served as the backdrop for films such as The Passion of the Christ and No Time to Die. Today, Matera is experiencing a thoughtful renaissance~ one you’ll come to understand more deeply during a private guided tour.

Our driver will bring us directly into the city, where we’ll stay at the five-star Aquatio Cave Luxury Hotel & Spa, a remarkable property carved into the ancient caves themselves. I’ve booked a €100 spa gift certificate for each person, allowing you to select your treatment (s) from the spa menu before our arrival. From facials to massages, the choice is yours!

During our stay, we’ll explore Matera with a knowledgeable local guide, gaining insight into both its ancient past and modern revival. We will also enjoy a bread-making experience in a local forno, learning the traditional method used in the region as we make fresh bread. For those who wish, there will also be the opportunity to walk across the river gorge to visit the ancient caves on the opposite side—an unforgettable perspective of the city. Matera is small, walkable, and endlessly atmospheric. On our final morning, a private car will transfer us comfortably to Bari Airport.