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Matera to Lecce

Puglia Cultural Walking Tour

6 DaysStarting at $6,495
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Overview

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.

Classic Journeys provides unbeatable access to experiences around the globe.”
Travel + Leisure

Itinerary Highlights

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• Explore Lecce, the “Florence of the South,” from a 16thcentury palace and stroll past Baroque facades and piazzas

• Follow coastal paths near Otranto, passing WWII bunkers and watchtowers, then linger over lunch at a countryside masseria above the sea

• Walk Matera’s canyon trails and Sassi lanes at eye level, with sweeping views from Parco delle Murgia

• Visit Altamura’s wheat country and join our friend Maria for homemade orecchiette, stuffed peppers, pecorino, and Pane di Altamura

• Share an alfresco lunch at Filippo and Chiara’s masseria, tasting cucina povera, estate olive oils, and homemade pasta

• Approach Alberobello on foot through vineyards and trulli-dotted countryside, then explore its fairytale conical stone houses with your local guide

• Stroll among ancient silverleaf olive trees to a family-run mill and learn how generations craft Puglia’s peppery, golden oils

• Unwind at a coastal masseria in Savelletri, with time for spa, pool, and sunset walks among olive groves

Download Full Daily Itinerary

Map

  • Starting Point:

    Lecce – 9:30 am – Lobby of Patria Palace

  • Ending Point:

    Brindisi – 12:00 pm – Brindisi airport
Itinerary Map

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Walking Level

  • Daily Mileage Options: 2-7 miles

  • Route Notes:

    The terrain on this trip includes a mix of paved and cobblestone streets in Matera, Alberobello and Lecce; as well as well-maintained countryside and coastal trails; and vineyard, olive grove and shepherds’ paths of compressed dirt and stone. The footpaths offer a selection of level, rolling and hilly terrain with some elevation gain and loss.
To See Mileage Daily, Download Full Itinerary

Dates & Prices

The earlier you book, the more options you’ll have and the lower your price. Secure your spot with a deposit of just $500 per person at the time of reservation. Plus, you can always change your mind — there’s no fee to transfer to a different trip before your final payment is due. Talk with one of our travel experts at 800-200-3887.

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Family Departure

Select our “Family Departure” to travel with other families.

Hotels

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. 

Patria Palace Hotel

Originally a princely palace built in the 17th century, this prestigious 5-star hotel has been restored, preserving its original beauty while adding every modern comfort. Each of the hotel rooms is personalized with original fresco paintings.

Aquatio Cave Luxury Hotel & Spa

Aquatio Cave Luxury Hotel & Spa is an enchanting 5-star property located in Matera, one of the world’s oldest cities. The luxurious rooms have been expertly designed in the ancient caves and enhanced with modern amenities for an unforgettable stay.

Masseria Il Melograno

A 17th-century fortified farmhouse turned five star Small Luxury Hotels retreat, surrounded by ancient olive groves, pools, and gardens. Interiors blend whitewashed stone, antiques, and contemporary comfort, with a serene spa and excellent Apulian restaurant creating a classic Puglia country estate feel.​

Masseria San Francesco

An intimate, authentic masseria in the countryside near Savelletri, surrounded by fields and olive trees, with suites opening onto stone courtyards and a tranquil pool. Guests enjoy warm hospitality, spa treatments, and easy access to nearby golf, beaches, and hilltowns.​

Borgo Bianco

A five star hilltop resort in traditional white stone masseria style, with sweeping countryside and Adriatic views, spa with indoor pool, and expansive outdoor pool terrace. Enjoy elegant rooms, excellent regional cuisine, and easy access to Alberobello.

What’s Included

  • Meals: All breakfasts, 2 lunches (1 cooking instruction), 3 dinners
  • Hotels: Award-winning boutique properties, thoughtfully selected for their exceptional location, design, history, and regional character.
  • Tour Leader(s): Expert guides who are your well-connected local friends and provide you access to people and places you wouldn’t find on your own.
  • Supplemental Experts: Additional regional guides and specialists on select tours.
  • Transportation: All land transportation as listed in the daily itinerary, including fares for trains, ferries, and other modes of travel.
  • Perfect Pairings Dinner: 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 experiences arranged just for you, as noted in the daily itinerary.
  • Admissions & Entry Fees: Entry to tastings, historic sites, and other scheduled activities listed in the daily itinerary.
  • Baggage Transfers: Upon arrival, we whisk you and your bags directly to your room—no waiting, no tipping.
  • Gratuities: All gratuities at hotels, restaurants, and for baggage handling.
  • Dedicated Guest Services Coordinator: Your pre-trip concierge and tour expert, available to answer questions and ensure you’re fully ready to get the most out of your tour.
Not Included: Tour Leader gratuities, travel to and from your trip’s start and end points, and any meals or activities taken independently.

Why Choose Classic Journeys

Travel + Leisure has awarded Classic Journeys the #1 World’s Best Tour Operator multiple times and says, “Classic Journeys provides unbeatable access to experiences around the globe.” Here’s what that access means for you.
  • 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.

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FAQs

Why is Classic Journeys the best tour company for Puglia tours?

If you want to experience Puglia at its most authentic, Classic Journeys is the best option. You’ll join a small group and walk cinematic footpaths through olive groves and trulli villages, discover people and places you’d never find alone, and eat like (and with) the locals—even cooking with farm families. Your expert local guides are your well-connected friends, opening doors to family-run estates, artisan workshops, and explorations of ruins, villages, and coasts that you’ll dream about long after you return.

Which places does the Classic Journeys Puglia itinerary visit?

Your Puglia adventure takes you from the fairytale trulli of Alberobello to Ostuni’s dazzling “White City,” Lecce’s Baroque architecture, the Valle d’Itria’s hill towns, and into Matera’s historic heart. You’ll walk through olive groves, visit ancient cave dwellings, soak up coastal views and savor local lunches with farm families. Each experience is handpicked, giving you up-close access to Puglia’s artistry, history, and flavors that only Classic Journeys can offer.

When is the best time to visit Puglia?

With a mild Mediterranean climate, Puglia is enjoyable to visit year-round. However, Spring (April–June) and autumn (September–October) are the sweetest seasons in Italy’s heel. Olive trees shimmer, wildflowers bloom, and villages are lively but uncrowded. You’ll walk in sunlit comfort, enjoying mild weather ideal for countryside strolls and cliffside ambles with your expert local guides leading the way.

How active is the Puglia cultural walking tour and is it suitable for mixed abilities?

On tour, you’ll walk between 2–7 miles daily at an easy, flexible pace—through olive groves, trulli lanes, cobblestoned towns, and scenic coastal paths. The terrain is a mix of paved streets and gentle trails, suitable for a range of abilities, and our guides can tailor the experience so every walker feels comfortable and inspired.

How many travelers are in each small group on your Puglia tour?

You’ll share incredible experiences in Puglia with a small group—usually 8-12 guests—so every moment feels personal, friendly, and flexible. With no more than 18 guests on tour, this cozy size allows special access and genuine camaraderie with fellow travelers and guides.

What are the start/end logistics for the Puglia tour?

Your Puglia journey starts in Lecce and ends in Brindisi, with easy access from both Bari and Brindisi airports. Classic Journeys whisks you and your bags directly to your room—no waiting, no tipping—and handles all land and luggage transfers between each stunning stop along the way for a seamless travel experience.