Discover Puglia Food, Wine & Culture Tour (September 1-9, 2026)

Discover charming towns, ancient history, and beautiful craftsmanship on this small group food, wine, and culture tour to Puglia + Basilicata.

What to expect

Surrounded by crystal-clear seas, Puglia is a unique combination of ancient history, beautiful craftsmanship, and welcoming locals who love to feed you! We’ll also visit Matera (Basilicata), one of the oldest cities in the world, and hear about its fascinating history. Enjoy Puglian food and wine tastings, cooking classes, sightseeing, artisan workshop visits, and have free time to wander on your own. Best of all, you’ll meet our friends and live like a local in this truly magical region of Italy!

Day to Day Itinerary

Day 1: Tuesday, September 1, 2026: Arrival in Puglia

Today is your arrival day at our beautiful Masseria in the Itria Valley. This historical manor farm has been transformed into a boutique accommodation surrounded by ancient olive trees and gardens. It will be our home base to explore this beautiful area of Puglia for the next 5 days. Trulli (traditional dry stone huts) enclosed by vineyards and olive groves stretch as far as the eye can see across this valley. From here we’ll visit some of Puglia’s most iconic towns and landscapes. 

Depending on your arrival flight, you’ll have time to relax before an evening welcome drink with snacks followed by dinner.

NOTE: The closest airport to our masseria is Brindisi Salento (BDS). Once we have your flight information we can arrange a private airport transfer upon request and/or pair you with others arriving at the same time to save costs.

Day 2: Wednesday, September 2, 2026: Polignano a Mare

Today we’ll travel to the striking town of Polignano a Mare. This picturesque village, known for its dramatic cliffs, affords stunning panoramas of the Adriatic Sea. At the port, we’ll embark on a boat to explore the sea caves hidden underneath the town. As the boat ducks in and out of the caves, imagine the centuries of smugglers who used them to hide their goods. On this boat trip, there will be a chance for a swim for those who would like to take a dip in the crystal blue waters of the Adriatic.

The town is an absolute must-see and is home to some of the best seafood restaurants in the area. Indulge in a seafood lunch before taking a walk through town to explore the shops or wander to the town’s beach. In the afternoon we’ll return to the Masseria to relax before dinner.

Day 3: Thursday, September 3, 2026: Ostuni + Ancient Olive Groves

Today we’ll head to Ostuni. This wonderful medieval village is full of narrow streets and whitewashed houses laid out in a maze reminiscent of an Arab casbah. You’ll have free time to walk in the old town, with its picturesque views, artisan shops, and little cafes. For those interested, a small archeological museum in Ostuni tells the story of a pregnant Stone Age woman (the eternal Earth Mother), whose 28,000-year-old remains were discovered in a nearby cave. There is also a wonderful walk around the ancient city walls that offers beautiful views of the olive groves and the Adriatic Sea beyond.

Later, we’ll visit a nearby farm owned by our friends Corrado and Antonella. We’ll learn about these ancient, monumental trees, and how to taste olive oil with a critical approach before a homemade lunch of local specialties made by Antonella. After lunch we’ll return to our masseria for free time to relax before dinner.

Day 4: Friday, September 4, 2026: Alberobello Our Way

Today we’ll visit Alberobello, in the heart of the “Murgia dei Trulli.” A lovely spread of pinnacles announces Alberobello’s characteristic historic center, a UNESCO World Heritage Site. The old town center here is entirely composed of trulli, the traditional houses capped by conical-shaped, bare-stone roofs. Crosses, pierced hearts, and zodiac signs decorate the roofs, maintaining the air of mystery that surrounds them. 

Though Alberobello has been “discovered,” you won’t suffer the tourist crowds here! We’ll have a visit with our energetic friend, Mimmo, who grew up among the trulli. Mimmo is now a local tour guide and enoteca owner with all things Alberobello coursing through his veins!!! He’ll take us to the secret spots that only a local would know. After our tour, we’ll have lunch in the garden of one of his trullo homes—cooked for us by his mom and aunt. We’ll also have time to explore the town’s boutiques before we return to our Masseria with free time to relax before dinner. 

Day 5: Saturday, September 5, 2026: Grottaglie Ceramics & Cooking with Special Guests

This morning, we head to Grottaglie, a town with a ceramics district where pottery wheels turn ceaselessly in more than 50 craft shops. After a bit of free time to shop, we’ll visit one of Susan’s friends, a local artisan, Massimo. He’ll give us a tour of his nearby house, and you’ll hear the true story of a dream come true that has transformed his house into a de facto museum! After our visit, we’ll have lunch before returning to the masseria.

In the evening, we’ll enjoy a Taralli and Foccacia-making lesson at the Masseria. Puglia is known for exceptional focaccia made from ancient wheat. But then there’s Taralli. These crispy rings of heavenly crunchiness are a staple Puglian snack food and are never missing from an aperitivo. We’ll also enjoy a mozzarella-making demo with a local cheesemaker who will explain the process and show us how to tie the cheese before snapping off the end with a quick motion called “mozzare.” Dinner tonight will be the fruits of our labor.

Day 6: Sunday, September 6, 2026: Gioia del Colle + Matera

Along the way, we’ll stop in the Gioia del Colle DOC wine zone for a tasting, tour, and lunch at Cantine Polvanera Winery. The winery, with its cellar, excavated into 8 meters of limestone rock, is surrounded by a singular countryside, with typical dry stone walls, downy oaks, and vineyards. It derives its name from the Puglian dialect word, “POLVAGNOR,” the name given to the peasants who once produced coal here and whose skin was often dirtied by a layer of coal dust (polvere).

After lunch, we’ll head to Matera to overnight in the Sassi district, the part of Matera made up of ancient cave dwellings that are now a UNESCO World Heritage Site. We’ll check into our hotel, which is partially constructed from these very caves, before an afternoon tour followed by dinner at a local favorite restaurant.

Day 7: Monday, September 7, 2026: Matera & Lecce

Before departing Matera, we’ll have free time to wander, shop the many artisan boutiques, or join an optional multimedia presentation given by FAI about the fascinating history of the Sassi di Matera. You’ll enjoy lunch on your own before an afternoon departure for Lecce. Once in Lecce, we’ll check into our boutique hotel in the historic center for free time to relax before “apericena” at a local favorite enoteca. Apericena is the Italian word for a light dinner, but in Puglia, the term “light” needs to be taken with a huge grain of salt! Not only do the locals enjoy a good meal, but they also thrive on making sure others are well fed too.

Day 8: Tuesday, September 8, 2026: Artisans + Orecchiette

This morning we’ll have an optional visit to a local papier-maché atelier. This craft has been practiced for centuries in Lecce, and the studio is owned by three brothers, the latest artisans in the Riso family of multi-generational craftsmen. Afterward, you’ll have free time to wander with lunch on your own. In the late afternoon, we’ll have a cooking class with Susan’s friend, and local chef, Gianna. Our cooking class will include orecchiette-making, Puglia’s most famous pasta. We’ll dine on the fruits of our labor and end the evening with a local specialty that is something not to be missed while in Puglia.

Day 9: Wednesday, September 9, 2026: Arrivederci Puglia

Today is your departure day. After breakfast at our hotel, we’ll say arrivederci until our next adventure in La Bel Paese.

NOTE: We can arrange a private airport transfer upon request and/or pair you with others arriving at the same time to save costs.

PLEASE NOTE:

1. Although every effort is made to adhere to the stated tour itinerary, itineraries are subject to change at any time due to unforeseen circumstances beyond the control of Via del Vino, LLC and its travel providers. A non-refundable deposit is due at the time of booking to secure your spot.
2. Our Puglia tour uses charming historic properties with a mix of rooms that are all unique and may vary in size and amenities. Rooms are allocated on a first-come, first-served basis according to need (doubles vs twin beds vs single supplement). Single supplement rooms are limited. Please let us know if you need twin beds.

Physical Requirements of This Tour:

• Walking unassisted at a relaxed pace on uneven pavements, hills, and stone stairs with only short breaks
• Standing for 2 hours for walking tours with only short breaks and limited seating available
• Negotiating stone stairs to access some hotel rooms without elevators (porters will assist with luggage)
• Getting on and off the minibus unassisted
• This tour is not suitable for guests with mobility issues

What’s Included:

• 8-Nights Accommodation in historic/boutique properties
• Transportation for all daily activities
• Daily breakfast
• 5 lunches and 8 dinners all include wine
• 2 cooking classes
• Guided tours in Alberobello and Matera
• Artisan Visits in Grottaglie and Lecce

What’s Not Included:

• Airfare
• Airport transfers (can be provided for an additional cost)
• Cash tips for local guides (optional)