When we ask our Italian guides where they'd most like to take our friends who think they know Italy on a walking tour we get one response: Puglia. And then they use their hands. To paint a vista of gnarled olive trees silhouetted against a lapis lazuli sea. To express the amazing sunlight. To sketch the saw-toothed skyline of a village comprised entirely of "trulli"—the conical stone roofs unique to the region. You should see a good Italian describe the food you'll find—pasta from the locally grown wheat, sea-fresh fish, peppery olive oil. The Italians love the heel of their boot and it's easy to see why. Especially since it's also a land where you're as likely to find a Baroque city as a family of shepherds tending 500 sheep. Best of all, Puglia passes the most important Classic Journeys test—it offers fine leisurely walking…elegant accommodations …and a glimpse into a region and culture that's not quite like any you've encountered before.
• Gather at your hotel situated among olive groves, then enjoy a scenic stroll through the nearby ancient Roman ruins and prehistoric cave dwellings.
• From cliff-side lodgings in Matera, explore nearby Alberobello — a local landmark and the largest collection of conically roofed trulli — a must-see.
• Walk through cinematic countryside to spend time with owners of a 17th century working farm.
• Visit a family of shepherds near Altamura where our hosts invite us into their kitchen to prepare and eat a typical local lunch of homemade orecchiette pasta, stuffed peppers and pecorino cheese.
• Amble in countryside known for its shimmering silver-leaf olive trees.
• Explore Lecce, the "Florence of the South," from our home, a 16th-century palace.
• Marvel at one of the world's largest mosaic floors, not far away in Otranto's cathedral.
• Journey on foot to visit architect friends and see their stunning renovation of an ancient farmhouse.
Starting Point:Lecce – 1:00 pm – Lobby of hotel in Lecce
Ending Point:Brindisi – 1:30 pm – Brindisi airport
Dates & Prices
The earlier you book, the more choice you’ll have and the lower your price. And you can always change your mind — you won’t be charged to transfer to a different trip before your final payment is due. Talk with one of our travel experts at 800-200-3887.Talk to an expert
Select our “Family Departure” to travel with other families.
Why Choose Classic Journeys
- Experience Puglia on foot and at eye level. Each day, join your guide on the most cinematic footpaths in the region, including along scenic canyons to iconic perched villages like Matera, through shimmery green olive groves and on working estates.
- Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, sharing their lifelong connections as well as engaging anecdotes about the history and culture of Puglia.
- Small groups that provide you unrivaled access. An average of 10 guests per departure means we can offer you special ‘only with Classic Journeys’ access to villages like Alberobello with its fairytale stone-roofed houses, a cooking instruction with a family on their farm that other companies cannot arrange because of larger group sizes, and walks with a olive oil maker on his estate.
- Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in Puglia, including a private estate that has been in the same family for generations, and award-winning properties that show up on World’s Best and Gold lists.
- Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of Puglia. From lunches with families on their farms and estates to coveted Michelin-starred restaurants, our meals offer you opportunities to explore native food traditions and fine dining.
- Handcrafted itineraries with all activities included. With our long-term friendships, we know Puglia more personally than anyone else. So you get thoughtfully curated itineraries that combine explorations of the villages, organic farms, archeological sites, and the people who know them best.
- Regenerative Travel that supports the history, culture, people and places you’re visiting with us in Puglia. We put our local currency into the pockets of the people who live where we travel. It’s your guarantee that you’ll have authentic, up-close experiences on your trip. Best of all, our person-to-person approach helps sustain their ways of life.
We spend years cultivating personal relationships with our hoteliers to provide you thoughtfully selected accommodations that reveal the true character of the region. Here is a sampling of our favorite hotels on this tour.
- Award-winning boutique hotels that provide you unlimited access to the people and places, culture and history you came to experience
- All breakfasts, 4 lunches (1 cooking instruction), 3 dinners
- Full-time experienced guide(s) who are with you throughout the trip and handle behind-the-scenes logistics
- Admissions to tastings, historic sites and other scheduled events as noted in the detailed daily itinerary
- Gratuities for hotels, meals, and baggage
- All land transportation during the trip
Above & Beyond Benefits
Perfect Pairings Dinners
- A special dinner prepared by one of our favorite chefs with a procession of wines tailored to each course.
Privileged Access Events
- One-of-a-kind access to remarkable people, places and activities arranged just for you.
Wine on Us
- In many regions, we uncork wonderful local wines at every dinner, compliments of Classic Journeys.
- When your group arrives, we whisk you and your bags to your room immediately. No waiting – no tipping.