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Originally from Toronto but now living in Italy, I’ve always been a traveler at heart. When I’m not planning your luxury European trip, you’ll find me hiking the Italian Alps or enjoying a lemon Spritz in Amalfi.
- from $4,376 PP
- 8 Nights
- Apr - Oct
- 2hrs from London / 9hrs from NYC
Explore one of Italy’s lesser-known regions, avoiding the crowds while enjoying everything from beautiful beaches along the Adriatic coast to rich history and mouth-watering cuisine. You’ll start in the city of Lecce, renowned for its magnificent baroque architecture, concluding in Matera with its Sassi area, an intriguing complex of cave dwellings that were carved right into the mountainside. Embark on tours led by expert local guides to learn the stories behind all the sights with plenty of time to relax and explore on your own. Along the way, expect comfortable, upscale accommodation that’s been hand-selected by our staff to ensure an ideal base.
Our Flexi - Promise
Low Deposit To Book
Book your trip with us and pay a reduced deposit with the rest 90 days before your departure
If you are not comfortable traveling, you have the right to cancel and get a refund up to 45 days before your departure
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No Change Fees
We will not charge you any admin fees if you would like to change your travel dates or destination with us
- 8 nights hand-selected 4- and 5-star accommodation
- Personalized planning
- Customizable itinerary
- 24/7 staff support
- Tour of Baroque Lecce
- Otranto Tour
- Tour of Polignano & Bari
- Tour of Martina Franca, Locorotondo & Alberobello with Lunch & Wine Pairing
- Sassi di Matera Tour with Tuk Tuk
- Luxury transfers as noted on itinerary
Day by Day Itinerary
Day 1 Lecce: Arrival into Bari Airport, Transfer to Lecce
Begin your journey with arrival into Bari Airport. Our driver will welcome you and provide a private transfer to your hotel in Lecce, the “Florence of the South,” known for its elegant baroque churches and historic sites dating back to Roman times. After getting settled in and refreshed, you might want to take a stroll to beat jet lag, enjoying a preview of this beautiful city and its enticing mix of old and new. Perhaps stop to unwind with a glass of wine and then pop into an eatery to sample orecchiette pasta, Puglia’s most iconic food. For those who still have the energy, this city offers lively nightlife too.
Day 2 Lecce: Tour of Baroque Lecce
Our local guide will bring you on a tour of Lecce’s many highlights, including impressive baroque architecture which led to its nickname, “The Florence of the South.” It’s like an open-air museum, with many magnificent palaces and churches. Dating back to Roman times, traces of its past can be seen in a 2nd-century Roman amphitheater with columns marking the end of Appian Way. Marvel at Santa Croce Basilica, built between 1353 and 1549, with a stunningly decorated façade and large rose window. You’ll see the former convent of Celestine monks, now the Government Palace, and enjoy about 90 minutes of free time in Piazza Duomo.
Day 3 Lecce: Otranto Tour
Join our driver/guide for a private tour of Otranto, a historic town that lies along the Adriatic coast. It offers an intriguing mix of history, architecture, and picturesque views, with its top attraction the 12th-century mosaic floor in the Romanesque cathedral that was consecrated in 1088. It also boasts a rose window, an interior featuring columns that are said to come from a temple of Minerva, and a crypt with 42 marble columns. A Chapel of the Dead with the 800 skulls of martyred citizens who were beheaded for not renouncing Christianity when Turkish pirates invaded in 1480 is a secret that lies within. After touring, enjoy 2.5 hours of free time for shopping, a cappuccino, or lunch on your own.
Day 4 Monopoli: Transfer to Monopoli via Ostuni
Get your bags packed and ready for a private transfer to Monopoli with a stop in Ostuni. Often referred to as the “White City,” the walled hilltop town stands out with its hilltop perch overlooking centuries-old olive tree groves that spread out toward the Adriatic Sea in the distance. Reminiscent of a Greek village, the whitewashed buildings are splashed with vibrant blue and green doors while bougainvillea hangs from windowsills. Continue to Monopoli, a city with Greek origins as its name belies. While it has a modern side that sprawls along the coast, it also has a charming historic center and long fishing tradition. After checking into your hotel, you’ll have the rest of the day to enjoy at your leisure. We’d highly recommend a stroll along the lungomare, a paved promenade running along the coast, edging the Old Town. From the old defensive tower, enjoy an awe-inspiring view and then head to one of the waterfront restaurants, many of which focus on fresh fish and seafood.
Day 5 Monopoli: Tour of Polignano & Bari
This morning your private driver/guide will bring you to picturesque Polignano, a coastal town built on top of limestone cliffs dotted with spellbinding sea caves. Many come to leap off into the Adriatic, a scene that’s mesmerizing to witness. You’ll get to stroll through to view the spectacular panorama of terraces and a lovely square with a clock tower and church. Enjoy free time before continuing to Bari to marvel at its famous Norman castle, a medieval structure surrounded by a moat that was filled and turned into a street. You’ll see the church of San Gregario and other landmarks before taking time for lunch on your own.
Day 6 Monopoli: Tour Martina Franca, Locorotondo & Alberobello with Lunch & Wine Pairing
Enjoy a three-in-one that starts by visiting Alberobello with your private driver/guide. Upon arrival to this famous town known for its trulli, whitewashed buildings with stone cone-shaped roofs built without mortar, you’ll meet a local guide for an inspiring tour. Discover this fairytale-like place where the locals constructed these temporary dwellings to avoid taxes as they could easily be knocked down at inspection time. Step inside one, visit a Trulli-style church and enjoy lunch at a unique Trulli-style restaurant. Continue to Martina Franca with its memorable maze of winding alleyways, whitewashed simplicity, and baroque extravagance. Discover more beauty in the hilltop village of Locorotondo, renowned for its winemaking and baroque architecture.
Day 7 Matera: Transfer from Monopoli
This morning you’ll be met by your private driver for transfer to the unique town of Matera, nestled among the cliffs in the Basilicata region. The “Sassi ” area is a UNESCO World Heritage Site with cave-like homes, hotels, and restaurants carved out of limestone rock, it’s the world’s oldest continuously inhabited settlement behind only Petra in Jordan. After checking into your accommodation, you can give your legs a workout by climbing the steep streets and stairways for a preview of the Sassi’s unearthly, ancient beauty. If it looks familiar, that might be because it was used as a film setting for Mel Gibson’s “The Passion of the Christ.”
Day 8 Matera: Sassi di Matera Tour with Tuk Tuk
Today you’ll get an insider’s look at the Sassi de Matera and its unique homes, including the opportunity to step inside Casa Grotta to witness firsthand how the early settlers lived. Believed to be some of the very first human settlements in Italy, dating back as far as 15,000 BC, for thousands of years there was no running water, let alone sewage or electricity. See the animal stables, a kitchen, and bedroom, along with a cave church. With so many steep steps to climb, you’ll appreciate the grand finale – a 30-minute Tuk Tuk tour that will allow you to discover more sights while giving your feet a rest.
Day 9 Matera: Departure
After more than a week of exploring some of the best of Southern Italy, it’s time to get your bags packed and ready to begin your journey home or for further travels elsewhere. If you haven’t made plans but aren’t ready to return, our travel experts will be happy to create a bespoke addition to your itinerary. Otherwise, you’ll be met by our driver for a private transfer to the airport in Bari where you’ll catch your flight.
What's not Included
- As we have clients from all over the world. Our itineraries do not include flights. If you would like us to include flights in your trip, we are happy to do so. Please speak to your travel specialist at the planning stage to include them.
- Gratuities for local guides
- We strongly advise all guests purchase comprehensive travel insurance
- Visas if required
Let’s get started making this itinerary yours.
Speak to experienced Destinations Experts about designing this itinerary around your budget and trip preferences
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The Best Guides
What makes our trips extraordinary is the unique immersive experiences we include. We pride ourselves in our black book of sought after expert guides, game rangers and local contacts who believe in our philosophy, unforgettable.
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