Join us for a historical, cultural, and culinary adventure to “the heel of the boot,” one of Italy’s least-exploited tourist destinations. The Salento Peninsula has been conquered and influenced by many ancient civilizations, from the Byzantine Greeks to the Romans, the Arabs to the Bourbons. Puglia has hundreds of miles of golden beaches lapped by azure waters, a breathtaking combination of whitewashed hilltop villages, and beautiful Baroque cities like Lecce and Bari. This is one of the most fascinating, history-filled destinations you'll ever visit. Puglia is ground zero for some of the most classic Italian dishes and many you've never heard of. All are mouthwatering. From the famous Pane di Altamura, an ancient traditional bread made in the hilltop town of Altamura since 1420, to orecchiette (ear-shaped pasta) with broccoli rabe or turnip greens to focaccia (yes, we've all had focaccia, but it's better here) to cartellate, a fried rose-shaped pastry flavored with honey or vincotto. You'll savor a multitude of delights over meals and get your hands dirty during two unique cooking classes. Vine is a vital part of this region. Here, you will find world-class wines, like the Nero di Troia, an unctuous red. The scenery vies with the food for sheer enjoyment. You're surrounded by water from the Adriatic and Ionian seas. The views are often dramatic. On this trip, you'll visit the UNESCO World Heritage town of Alberobello, staying in a Trulli resort hotel. A trulli is a conical-shaped traditional Puglian farmhouse. Later, in the town of Matera, you'll spend two nights in a cave hotel. These unique structures are only found in this region. Add to that the olive oil farms dotted with 1,000-year-old olive trees, and you've got the makings of a delectable excursion.
Here's a day by day itinerary of the trip to Puglia
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The combination of a 19th century palazzo and an authentic trulli makes for a uniquely beautiful hotel and a real step back in time but with added comfort and style.
A one thousand year old cave turned into a five-star hotel. Now that's alluring!
Since 1,500 Masseria il Frantoio has been the answer to travelers who have wondered where to stay in Puglia. Located in the countryside near Ostuni, this transformed ancient farmhouse in one of the most authentic hotels in Puglia, where culture and tradition are alive and well.
Meet Leigh- Intense Foodie, Lover of Italy, Wanderer, and guaranteed to offer you mint green tea.
Meet Jessica Fulton, your trip host based in Tampa, Florida. With an unwavering passion for travel, Jessica immerses herself in diverse cultures to create meaningful experiences. Balancing her life, she juggles a tech career by day and embraces the joys of motherhood to two children and two lovable doodles. Eager to share the food delights and cultural heritage of Puglia, Jessica looks forward to embarking on this exciting journey with you. Follow Jessica's adventures on Instagram
The Heel of the Boot of Italy
Dreamlike bays, stone villages, olive groves, wilderness, unique architecture and four UNESCO sites, each one is more fascinating than the next. Puglia has been named the "most beautiful region in the world" and for good reason. Scattered across the seashore and hilltop villages lie cathedrals, castles, whitewashed houses and flowered balconies. Puglia's captivating charm and delicious rustic food should not be missed.
Lodging at unique hotels
All guides, experts and entry fees
All in-country transport including airport transfers
A small group experience
All meals as indicated in the detailed itinerary
A GG2W gift
Guided tour of Conversano
Guided walking tour of Conversano
Tour of the whitewashed town Locorotondo
Tour of an olive oil farm
Visit to a legendary bakery to discover how local bread is made
Cooking classes
Guided tour of the historical center in Lecce
Local wine tour
Additional wine, beer, or spirits beyond what is offered at meals.
All personal souvenir purchases
Travel and Medical Insurance (required)
Round Trip Airfare to Bari, Italy
The trip officially starts on May 9, 2025 in the morning. If you’re traveling across an ocean to get to Italy, consider arriving a day or two early so you have time to relax and adjust to the local time zone. If you do decide to arrive early, let us know and we’ll help you with arrangements if you like.
Fly into Bari International Airport-Karol Wojtylat. If you plan to see more of Italy you can fly to any other major airport and take the train to Bari. If you need assistance with trains let us help.
Other nearby airports include Brindisi (BDS) (105.3 km) and Dubrovnik (DBV) (196.4 km).
We will have a Zoom call about six weeks before the trip starts to discuss all that information and give you a packing list. Here is a great website that we love that will help you with packing and travel trips.
The weather in Puglia in May is dry and warm. It's the start of the summer season with an average high temperature 71°F. Evenings are mild, the sea is now nudging 55°F and it's one of the driest months with only 1.5" of rain falling over a handful of days.