Swirling Adriatic and Ionian seas in hues of deep blue, heirloom olive orchards stretching to the horizon, whitewashed coastal towns gleaming in the sun—this is the “heel” of Italy, a world apart from the north. Our hikes bring us across traditional shepherds' trails and along spectacular coastal paths where the sea and the sky seem to meet. Along the way, we'll visit charming hill towns and ancient ports. Our final treat is a three-night stay in a historic hotel in the unforgettable World Heritage Site of Matera. As always, we'll eat locally and well—olive-tasting in the Itria Valley, sampling the deep red Primitivo wines in Manduria, and tasting the bounty of the sea.
Arrive: Bari, Italy
Depart: Bari, Italy
Pricing below is per person and based on double occupancy. The earlier you book, the more choice you’ll have. WT also has the most generous cancellation and transfer policies in the industry, we make it easy if you change your mind. Have a small group of your own? Take over an existing date or choose your own. You’ll have your own private guide–and the adventure–all to yourselves!
$600 due at time of reservation
90 days prior to departure: Balance
Up to 91 days prior to departure: No Charge!
61-90 days prior to departure: 25% of trip cost
46-60 days prior to departure: 50% of trip cost
45 days or less: 100% of trip cost
Scroll through our signature accommodations for this trip below. Although it is highly unlikely, we may make substitutions when necessary.
Days 1-2 (2 nights)
Days 3-4 (2 nights)
Just a short walk from Otranto's historic center, this hotel has modern guest rooms and a rooftop terrace with harbor views. The hotel's interior is decorated with museum-quality maritime artifacts collected by the owner.
Castrignano del Capo, Italy
Days 5-6 (2 nights)
The Hotel Terminal is set on a private beach just steps from Santa Maria di Leuca's harbor and offers a rooftop terrace and spacious guest rooms with ocean views.
Days 7-9 (3 nights)
Tucked away just steps from the Piazza del Duomo is Palazzo Viceconte, a splendid historic palace turned hotel. Fourteen guest rooms are uniquely decorated and have views of the courtyard or Sassi of Matera. Relax on the terrace, wander through the halls (the hotel has beautiful collection of art displayed...
Wilderness Travel Trip Leaders have a passion and a joy for creating an unforgettable journey. We are extremely proud of them and the incredible travel experiences they make possible. For more information, including client comments about them and which specific trips they will be leading, please click on their profiles below.
Gianluca CanalicchioView Profile
Irene De BenedictisView Profile
JoAnn LantzView Profile
Daniel WindhamView Profile
Leila ThompsonView Profile
You need to be able to hike on uneven surfaces, occasionally downhill over loose rocks, so good balance is important. The hikes explore a mix of terrain, from dirt roads to paths across rolling hills to ancient stone staircases, which can be quite steep. The trip is designed for those who have at least some hiking experience. Please note that the hiking can feel more demanding at times because the weather can occasionally be hot, even in fall when we make our journey. Sturdy, well broken-in hiking boots are best for some of the rural trails, though walking shoes may be suitable for some days.
For maximum enjoyment of the trip (and the wonderful scenery, food, and wine that are a part of it), we recommend you make a special effort to be in good physical condition. Daily brisk walking and/or regular hiking (or using a stair-climbing machine at your gym) are excellent preparatory exercises.
Our hotels are chosen for their local history and central location. Although rooms in European hotels are not always of uniform or international size, our leaders try their best to assign rooms in a fair way so that all participants experience an equal advantage throughout the trip as a whole.
Please note that in Europe, the dinner hour is considerably later than what it is in the US. We do our best to secure early reservations for our groups, but most often the evening meal will be at 7:30 pm.
Luggage is transported for us by van, so it is always possible to ride in the van if you wish to opt out of a day's hiking. We will carry just a daypack with water bottle, sunscreen, camera, and anything else you want with you while on the trail.
"The trip was amazing. We loved every minute of it: lots of culture, hiking (of course,) and wine and food."
"Your Puglia trip is just wonderful. We loved the itinerary, the culture, and all that entails, and the local guides were fabulous."
"Fantastic trip in a interesting area. We loved the food and wine. Our trip leader, JoAnn, made us all feel extremely welcome. We immediately felt comfortable with her."
"Great fun. They don't call it "Eatily" for nothing! Lovely hikes."
"This trip far exceeded our expectations. The itinerary was superb and the guides were terrific. The balance among hiking, city tours, and wonderful meals was perfect. The two days in Matera were magical."
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Our Area Specialists know every detail about our tours. They will be happy to answer any questions and help you choose the journey that’s right for you. Contact us to learn more or book your trip today!
Submit the form below to download itinerary
With more than 200 different adventures to choose from, we want to help you find the trip that’s right for you. Our Trip Level system ranks each trip in two ways: a number rating from 1 to 6 according to the activity, and general travel rigors. 1 is the easiest and 6+ the most difficult—see descriptions below for explanations of each number. A plus (+) sign means the trip is a bit more strenuous than other trips of that level. The detailed explanation of each trip—below the bar with the number rating—is perhaps more important, specifying activities, altitudes, hiking, and travel conditions. The Detailed Itinerary, available by download or mail, gives further information. Our Area Managers can also answer questions and guide you to the trip that best suits your interests.
Level 1 – Easiest
Non-camping journeys, optional walks, little elevation gain or loss.
Level 3 – Moderate
Half- to full-day hikes (3-6 hours) over rolling countryside on most days, occasional steep trails. Many of our hotel-based walking tours are in this category, as are our snorkeling adventures.
Level 5 – Strenuous
Full-day hikes (4-8 hours), mountainous, steep terrain (hiking up or down as much as 3,500 feet) on many days. Trips with hiking at average altitudes of 10,000 to 12,000 feet are in this category.