The trip in a nutshell
8 days/7 nights
Our tour in Puglia will warm your soul and remain among your most beautiful memories.
A ride along a country path among millennia-old olive trees, getting lost in the lively alleys of an ancient village, plunging from a cliff into the blue of the transparent sea, mojitos and laughter in a beachfront cocktail bar, the discovery of authentic dishes, the ancient silence inside a Baroque church, the sense of freedom dancing at the best electronic music festivals.
Describing Puglia in a few words is not easy; it is all this and much more. It’s a Southern region, known as the “Heel of Italy,” where diverse cultures, old and new, sea and hills, cities and small villages meet.
Among the main destinations is Alberobello, a UNESCO heritage site, a town known for its trulli, unique world architectures that make it seem like a fairy-tale place; there’s the elegant “white city,” Ostuni, with its center entirely painted white, shaped like a wedding cake; Polignano a Mare, perched on the rock and with its breathtaking views of the sea, is one of the most scenic cities in Puglia; there’s the elegance of Lecce, where Baroque triumphs; a few kilometers from the Puglia border, there’s Matera, UNESCO heritage site and European Capital of Culture in 2019, famous for the Sassi, ancient dwellings carved into caves.
Trip type
The keyword in Puglia is: relaxation. In this tour, we’ll embrace the relaxed pace of life of the locals, chatting in a square or sipping a glass of wine by the sea, without missing the many architectural and natural beauties that this beautiful Southern region offers.
Physical rating
For this tour, you don’t need significant athletic preparation. It’s enough that you are accustomed to medium-length walks. Special equipment is not necessary either. You simply need to train your gaze for beauty.
Entry requirements
Visas: Generally, American, Australian, British, and Canadian citizens traveling to Italy for stays of fewer than 90 days usually do not require a visa. However, there could be exceptions, and it remains the traveler’s responsibility to verify visa requirements. For more information please visit the Italian Government website. Starting from 2025, non EU citizens will need ETIAS to travel to Europe.
From Bari to Lecce, passing through the most romantic places in Puglia.
$5,498.00
Single room +$1,374.50
You can reserve your spot with a deposit. Select this option from your trip summary.
What’s included?
7 nights in 16th century farmhouse with pool – Masseria Montepaolo
7 Breakfasts, 5 Lunch, 7 Dinners
Local Guides and 1 Gay Up Travel Host from beginning to end of tour
Air conditioned
Private tour bus throughout
Transfer from Bari Airport or train stations on the first tour day, and back to Bari airport on departure day.
Cooking class in a masseria
Wine tasting and visit to a vineyard by the sea
Olive oil tasting
Boat tour
Visit to an ancient Sasso
Mozzarella making
Gratuities for hotel porters, drivers, and guides
A $50 USD donation to The LGBT Asylum Project to support the resettlement of LGBTQ+ refugees.
What isn’t included?
International flight
Travel insurance is mandatory for all travellers.
Gratuities for Group Leader (budget approximately $50-$100 USD)
Other items of a personal nature (Medical expenses, drinks, laundry, etc)
Anything not mentioned above under “What’s included?”
DAY 1
- Get ready for an exciting start!
- As you touch down at Bari airport…
As you touch down at Bari airport , our dedicated driver will be ready to escort you to Masseria Montepaolo. Nestled in the picturesque countryside of Conversano, just a stone’s throw from the Adriatic Sea, this heaven awaits. After settling into your rooms, join us for a tour presentation—let’s break the ice over a fabulous glass of wine! Following a quick spin around our marvelous masseria, we’ll in a delectable welcome dinner featuring regional delights.
DAY 2
- Conversano and Polignano a Mare
- Wake up to a new day filled with adventure!
After breakfast, we’re off to explore the medieval charm of Conversano, a mere 10 minutes from the masseria. Conversano has a thousand-year history and has been one of the most important centers in southern Italy. With its Norman-Aragonese castle, its cathedral in the Romanesque-Apulian style, megalithic walls, monasteries, and numerous squares, it attracts tourists from all over.
Right after we’ll head to Polignano a Mare. Perched on a 24-meter high cliff, the old town boasts mesmerizing views of azure seas and dazzling white houses. The old town, adorned with charming balconies and picturesque streets, is an absolute gem.
Polignano a Mare is even more beautiful when seen from the sea. We’ll take a wonderful boat tour from which we can admire the numerous caves upon which the town is nestled. After the boat tour, we’ll enjoy a seafood lunch at a traditional restaurant. And the excitement doesn’t end there – tonight, we’re off to Conversano for a group dinner featuring mouthwatering local dishes!
DAY 3
- Locorotondo and Alberobello
- Trulli houses, circular towns and mozzarella making.
Today will be an intense day full of emotions. Our first stop will be Locorotondo, one of the three towns that form the Itria Valley, filled in trulli is one of the most appreciated areas of the region. Locorotondo owes its name to its circular shape that has been preserved for over 1000 years. We will be fascinated by its sloping stone roofs, its all-white houses, and the flower-filled balconies.
Right after visiting Locorotondo, we’ll head to a dairy farm to make mozzarella starting from milk! Making mozzarella with your own hands and eating it freshly made will be an unforgettable experience. We’ll have lunch here with a variety of cured meats and cheeses made on the farm, flavors you’ve never tasted before. Guaranteed!
In Alberobello, we’ll explore a charming labyrinth of streets filled with trulli, the traditional conical dwellings of Apulia. Believe it or not, there are a staggering 1,400 of these unique structures scattered across the two districts! Declared a UNESCO World Heritage Site, they stand as a singular symbol of local culture and architecture. Trulli are dry stone constructions, built without cement. As we wander through this fairy-tale town, we’ll not only feast our eyes on its enchanting beauty but also uncover the history and evolution of these captivating buildings over the centuries. It’s a truly fascinating tale!
Tonight we’ll stay at the masseria, perhaps by the pool, and enjoy a light dinner.
DAY 4
- Monopoli
- Hold onto your taste buds for a flavor-packed day!
Today we start our day by visiting Monopoli, a town overlooking the Adriatic coast. Its historic center is entirely made of tuff, a yellow ocher marine stone, and is a maze of narrow streets that lead to the ancient harbor of the city, Baroque-style Cathedral, and to the castle of Charles V. The walls that once protected the inhabited center are still clearly visible, surrounded by a beach of golden sand.
After exploration the town of Monopoli, we’ll have an extraordinary cooking class, unraveling the secrets of Apulian cuisine. Get hands-on with panzerotti crafting, savor freshly baked focaccia, and relish the richness of homemade parmigiana. Afterward, retreat to the masseria for relaxation or opt for the soothing waters of the jacuzzi.
As night falls, we’ll go to into town for a culinary delight – savor the best Neapolitan pizza.
DAY 5
- Ostuni
- The old underground oil mill and “White City.”
The first stop of the day is dedicated to discovering olive oil. We’ll visit an ancient farmhouse surrounded by olive trees that are up to 4000 years old. We’ll uncover the secrets of oil production and learn about all the steps, from harvesting to pressing. Inside the underground oil mill, we’ll participate in a blind tasting of various olive oils and emerge as true experts.
Right after, we’ll head to Ostuni. Ostuni, known as the “White City,” enchants visitors with its white houses clinging to the hillside, creating a striking contrast against the azure sky of the Mediterranean. Renowned for its intricate maze of narrow and winding alleys, Ostuni boasts a millennia-old history reflected in its monuments and churches. During the guided tour, we’ll explore the historic heart of the city, strolling along its cobblestone streets and admiring Moorish and Baroque architecture. From the hilltop, we’ll enjoy breathtaking views of the surrounding landscape, allowing ourselves to be enchanted by Ostuni’s timeless beauty.
Our return to the masseria marks the beginning of our next immersive experience: il fornello! This authentic local tradition invites us to partake in a unique ritual—visiting the local butcher, hand-selecting our preferred cuts of meat directly from the counter, and then settling in for a delightful feast.
DAY 6
- Otranto and Lecce
- The queen of baroque and the bridge between east and west.
Today’s first stop takes us to Salento, the southernmost part of Puglia, precisely to Otranto. Its charming historic center overlooks crystalline waters and golden sandy beaches. Encircled by walls and dominated by the majestic Aragonese castle, it’s a labyrinth of narrow alleys and picturesque squares. Being the easternmost point of Italy, Otranto has always been a bridge between the civilizations that have succeeded each other in the Mediterranean and preserves their testimonies. One example is Otranto’s cathedral, with its magnificent mosaics and the famous mosaic floor, that tells millennium-old stories of faith and art.
Immediately after the visit to Otranto, we will head to a seaside winery, where we will tour the vineyards growing with the sea breeze they overlook. We’ll enjoy a wine tasting with truly special wines. Uncorking their classic method will make us smell the sea.
Now it’s time to head to Lecce, the “Florence of the South,” the queen of the Baroque. Its grand historic center is accessible through beautiful baroque doors made of intricately carved tuff stone, giving us immediate insight into the city’s majesty and elegance. The historic center is a labyrinth of cobblestone streets, elegant squares, and ornate churches, a testament to the art and architecture of the 16th century. During the guided tour, we’ll admire the grandeur of the Basilica of Santa Croce, the majesty of Piazza del Duomo with its famous bell tower, and the hidden treasures of Palazzo dei Celestini. But Lecce also has a Roman heritage, with two Roman theaters, the most important of which is located in the center of the main square. With its monuments, noble palaces, and extraordinary churches, the city center is an open-air museum!
DAY 7
- Matera
- Get ready for a grand finale in Matera, known as ‘La città dei Sassi’!
Matera, the city of the Sassi, offers a truly unique experience. Located in the Basilicata region, Matera is renowned for its ancient neighborhoods nestled in the limestone rocks of the Gravina di Matera. With its 10,000 years of history, Matera is the third oldest continuously inhabited city in the world. We’ll explore this incredible labyrinth of houses carved into the rock, winding streets, and millennia-old rock churches. We’ll admire the ingenuity of the rock architecture and uncover the fascinating history of how people have lived here for centuries.
Right after the visit we’ll have lunch in an actual cave that is now a great restaurant.
Back at the masseria and well-rested after the long day, get ready for the evening. We’re going to savor our farewell dinner at a sublime seafood restaurant, nestled right by the sparkling sea in Monopoli. In the evening, Monopoli transforms into a lively and vibrant city. Get ready for an evening of joy, laughter, and cherished memories!
DAY 8
- Departure
- It’s time to bid Puglia farewell!
Our final morning in Puglia begins with a farewell breakfast at the masseria. A transfer awaits to take you to the airport/station for flights to Rome and beyond. Note that, depending on flight schedules, an overnight stay in Rome could open up diverse options for connecting flights to your respective destinations. See you the next time!
