Overview
Classic Journeys provides unbeatable access to experiences around the globe.”
Travel + Leisure
Map
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Starting Point:
Lecce – 1:00 pm – Lobby of Patria Palace -
Ending Point:
Brindisi – 1:30 pm – Brindisi airport

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Walking Level
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Daily Mileage Options: 2-7 miles
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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.
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.
Talk to an expert
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.
What’s Included
- Meals: All breakfasts, four lunches (one cooking instruction), and three 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.
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By Classic JourneysFAQs
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 guide 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.