• Puglia Walking Tour Italy
  • Puglia Walking Tour Italy
  • Puglia Walking Tour Italy

Puglia Walking Tour


Our Puglia Walking Tour is designed to show you both the key sights of Puglia, and combines this with a series of walks that get you off the beaten track. Our walks take you through the countryside amongst olive groves and trulli houses, through vineyards alongside dry-stone walls. The walks allow you to get a close up feel for the land, the people and the traditions.

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Tour Highlights

  • A series of walks that take you through areas where you are immersed in the untouched and traditional areas of Puglia, with many centuries of history that reveal itself to you as we pass through at a pace allowing you to appreciate the smaller details
  • The UNESCO World Heritage sites of Alberobello (with its conical trulli houses) and Matera (with its cave houses)
  • Key locations such as Ostuni, Polignano A Mare, Lecce, Monopoli, Locorotondo
  • Enjoy a range of local food along the way, each day we stop in for lunch at good restaurants where we have 3-4 courses of the wonderful Pugliese cuisine

small group walking tour Puglia Italy

Puglia Walking Tour

  • This walking tour is a balance between the more active side – the walks – along with enjoying the cuisine, and visits to a range of interesting places. Generally we walk in the morning, stop for lunch in a restaurant, then visit other places in the afternoon
  • The walks are fully guided (no need to spend frustrating hours looking for the path!)
  • We stay for the week in one place, on a 17th century country estate that has been tastefully developed into a 4 star boutique hotel
  • Small groups, maximum 14 people
  • This is the trip that you’d design for yourself. We are Italy... with pleasure
  • This 7 day tour starts and finishes in Bari

small group walking tour Alberobello Italy

What our customers say about Italy With Pleasure:

“Everything was perfect! They packaged the hotel, all meals, daily tours to a variety of very special and interesting sites, and handled all of the myriad of details seamlessly. The agency is very customer-service focused and was a pleasure to work with. I highly recommend this tour company. Italy With Pleasure gets 5 stars!”

“I am widely travelled and have never been on a tour before so went with some trepidation.It was the absolute highlight of my travels in Italy and definitely the best food I had the whole time. I cannot recommend Italy with Pleasure more highly don't even think about it just book with them you will not be disappointed I am sure.”

“Our time travelling with ‘Italy with Pleasure’ was our best experience. Believe all that they say in their brochure .. family run, hands on and very professional. Their standards are high and they are very responsive to everyone’s needs. They source excellent restaurants... way beyond our experiences with other companies we travelled with. We highly recommend this company, have mentioned it to friends and fellow travellers”

“The itinerary was well organized and done at a comfortable pace: touring in the morning followed by mouth-watering lunch featuring the specialties of the area as well as fine wines of the area. All of the restaurants were excellent as was the food. It was a wonderful week and I will have many fond memories of my stay. This tour is a gem and I highly recommend it!”

“The tour group was quite small, 8 people all delightful. We were driven to some very interesting towns and other sites, where guides introduced us to the art and history... The tour was full but not too intense so we felt we had enough time to enjoyed the excellent food and wine which were highlights of the tour for us. I wholeheartedly recommend this tour.”

“The places that we visited were fascinating and very unique, and the food and wine was delectable. I didn't know what to expect of the trip, but it more than fulfilled any hopes that I had for a great week. Everything was well organised and the atmosphere was friendly and relaxed. I can thoroughly recommend the tour.”

“The way the tours are organised is very civilised. After a morning tour, always interesting in itself, we adjourn to a local restaurant for a late lunch and to experience the range of local foods cooked superbly. This tour stays in one place and each day we were escorted in a mini bus to our destination. A most enjoyable experience and well organised with a personal touch.”

Puglia small group walking tour Italy

Puglia small group walking tour Italy

Puglia small group walking tour Italy

Distinctive character, unique locations

During this tour you stay in traditional ‘massseria’ accommodation. A ‘masseria’ is a large farmhouse, and previously these were fortified, largely self-contained rural centres. The masseria, where you will stay, Masseria Salamina has been tastefully renovated as a boutique accommodation provider -see www.masseriasalamina.com.

By staying in the masseria you will be directly experiencing Puglia’s history. Set amongst olive groves and fig trees, the buildings were constructed in the 17th century. The property was established as an agricultural enterprise even earlier, and it is still operating as a farm. Around the grounds you will see numerous aspects of times gone by, giving an insight into the lifestyle here in centuries past – you are immersed in history.

But we don’t forget the needs of the present! The masseria offers all you would expect during your time here, such as wifi and a swimming pool. And as well as our other restaurants during the week, we also dine in the masseria’s own excellent restaurant which serves food grown right on their own organic farm.

Southern Italy Best of Puglia tour accommodation

Some reviews of our tours:

“Loved strolling through the gentle hills and valleys of Puglia, past trullies, individual plots for olives and almonds, wild flowers including orchids and vibrant red poppies. Travelling to towns such as Ostuni, Lecce, to the historic centres where we strolled though lanes taking in the sites and visiting churches, etc. The UNESCO town of Matera, with cave houses and cave churches hewn from the rock face of the deep ravine, was a highlight as was the 3-4 course lunches we had everyday.”

“Puglia is one of the real hidden treasures of Italy I think. Not too crowded or filled with tourists... I travel independently and had never done a tour before. This was just fantastic. Thoroughly recommend. Plenty of spare time and wonderful personal touches. A rare treat.”

“Everything was perfect! They packaged the hotel, all meals, daily tours to a variety of very special and interesting sites, and handled all of the myriad of details seamlessly. The agency is very customer-service focused and was a pleasure to work with.”

“The tour was absolutely fabulous. I was able to see and experience things that created once in a lifetime memories. Riccardo was phenomenal. He made sure that our trip was perfect. Any question or request we had, he worked hard to answer/meet. He was so upbeat and fun while dealing with all of our varied personalities! Thanks again for a trip of a life!”

“Everything was perfect! They packaged the hotel, all meals, daily tours to a variety of very special and interesting sites, and handled all of the myriad of details seamlessly. The agency is very customer-service focused and was a pleasure to work with.”

“The tour was terrific as was the hotel accommodation, and Andy was the best! It was well organized and we didn’t skip a beat. That last night at the farmhouse was memorable and the perfect send-off. The tour guides in each of the cities we visited were well informed and did a great job explaining what we were seeing. I highly recommended Italy With Pleasure to people I know that might be interested in travel to Italy. The small group size, and in our tour, Andy, is what makes it happen.”

See these and other reviews on Google Reviews, TripAdvisor and other review sites.

Day 1 - Buongiorno Puglia!

We meet in Bari, the main city of Puglia, and here we start our discovery of the region.

Our first stop is Polignano a Mare on the coast nearby, an impressive town clinging to a promontory suspended above the Adriatic’s turquoise waters.

With a history spanning back to the 4th century BC as a Greek settlement, Polignano a Mare is a charming town centred around the Piazza Vittorio Emanuele. Polignano a Mare encircles a pebble beach, nestled in a cove between rocky cliffs.

We advise keeping your camera at the ready!

We reach the Masseria Salamina, where we stay for the week. Set amongst olive groves and fig trees, the buildings were constructed in the 17th century. Around the grounds you will see numerous aspects of times gone by, giving an insight into the lifestyle here in centuries past – you are immersed in history.

The property was established as an agricultural enterprise right from the start, and it is still operating as a farm. They grow a wide range of produce, including wheat, vegetables, honey, and olive oil.

Tonight we dine together, having our first introduction to the cuisine of Puglia.

Throughout the week meals are in restaurants designed to showcase the region’s cuisine, with the specific venues all carefully selected by us. This is in order to provide a variety of food styles over the duration of the tour.

Meals included: Dinner (4 courses including wine)
Polignano a Mare small group walking tour

Polignano a Mare small group walking tour

Day 2 - Alberobello and Trulli

In the morning on our first walk we start to explore the fascinating area that you are based in. Starting out in an area of oak forest, the walk opens out to an area that has many working agricultural enterprises, vineyards, and the numerous small-holdings of the local community.

We start to see the trulli, unique to this area, and a taste for what is to come this afternoon in Alberobello. We see evidence of how people lived here in times past, such as ‘cisterna’ underground tanks for water collection, and ‘aia’ raised platforms for the drying of grain.

As we walk through the countryside you will have the history of the area explained to you, while seeing first hand the combination of age-old practices along with more modern technology used to work this land today.

In the afternoon we visit the picturesque Alberobello. First we have lunch in what used to be an olive oil mill from back when this town was a simple agricultural centre. After lunch we explore Alberobello. This UNESCO World Heritage site is a unique town with streets lined with 'trulli'. In fact it is known in Italy as the “Capital of trulli”. Trulli are small stone houses with a distinctive conical roof, built 300-400 years ago.

By walking along its narrow streets, you will be fascinated by the magical and fairytale atmosphere of this place. We explore this town together, and learn about why and how these dwellings were built, and about the cryptic symbols painted on the roof-cones. You’ll also have free time to browse the shops of Alberobello and to wander around.

Walking Details:

The walk is fully guided. Total Distance: 5 miles / 8 km. Duration of Walking: 3 hrs. Terrain: Well formed track, slight inclines.

Meals included: Breakfast, Lunch (2 courses including wine)

Puglia Small Group Walking tour Alberobello Italy

Puglia walking tour Alberobello experience

Day 3 - Ostuni: The Ancient Plains

After a short drive toward the coast, we begin today’s walks and start to really get an understanding of the depth of history that we are surrounded by. Walking first through open plains, we come across abandoned dwellings – in this area evidence has been found of inhabitation since Neolithic times.

Part of the route we walk today follows the route of the ancient Roman road called Trajan’s Way. This was built to connect Rome with the port of Brindisi further south in Puglia, and the trade routes that extended out from there. For lunch we visit Ostuni, known as “la città bianca” (the white town). Ostuni is a cluster of whitewashed buildings perched on a hilltop overlooking the coast. Walking through the narrow streets is like being in a forgotten time, evocative and ancient, looking out over an expanse of olive trees. We arrive at our lunch venue, enjoying the time to recharge and relax.

After lunch we visit a 'masseria'. A masseria is a historic farm centre, originally with all the estate's workers living in the fortified buildings. Nowadays some of these estates are still agricultural enterprises, while others have been converted into boutique lodges. The masseria that we visit still produces organic extra virgin olive oil from trees that are many centuries old. This land has been worked for thousands of years - we are shown the remnants of the ancient Roman agricultural production here, along with items of habitation from the middle ages through until modern times. After seeing the ancient trees we enjoy a degustation of a range of olive oils. This allows us to compare the different tastes from the olive varieties grown here.


The walk is fully guided. Total Distance: 7.5 miles / 12 km. Duration of walking: 4 hrs. Terrain: Well formed track, some country roads, flat.

Meals included: Breakfast, Lunch (3 courses including wine)

Southern Italy tour experience

Puglia Walking tour olive grove

Day 4 – Lecce: The Marvels of Elegant Baroque

Today we travel to Lecce, a city that flourished in the 17th century when elegant baroque buildings were built by the ruling classes. The baroque style features ornate decorations on the facades of churches and palaces.

This day is not a hiking day – we do a walking tour of central Lecce, but actually this day gives your legs a bit of a rest.

On our private walking tour around Lecce with a local expert guide to have the key sights explained to us. The baroque style here is distinct from that in other parts of Italy, both stylistically and in the use of beige local stone.

As well as the architectural and historical features, Lecce is an elegant town in which to indulge in more modern pleasures. There are many interesting boutiques and cafes, and the piazzas are full of life in this important southern Italian centre.

After some free time in central Lecce we have lunch in a local restaurant, where we experience the food specific to this part of Puglia, called ‘the Salento’. We dine on foods such as ‘ceci e tria’ (a type of pasta dish only made in Lecce), and of course we finish with the delicious ‘caffe leccese’ (espresso on ice with sweet almond syrup).

In the evening we visit to nearby town of Monopoli. This is a free evening, we give you details of the town and let you enjoy the atmosphere independently. Monopoli is situated on the coast, has great sea views, and vibrant piazzas that are perfect for people watching.


The walk is fully guided. Total Distance: 3.7 miles / 6 km. Duration of walking: 2 hrs. Terrain: Paved and flat (city walk gives your legs a break!)

Meals included: Breakfast, Lunch (3 courses including wine)

Puglia walking tour Italy

Puglia walking tour Monopoli Italy

Day 5 – Matera: A Step Back In Time

This morning we travel to the town of Matera in the neighbouring Basilicata region. Visiting Matera, a UNESCO World Heritage site, is like a step back in time. In fact this is one of the oldest continually inhabited settlements in the world. The oldest cave dwellings go back to the Bronze Age.

We spend the morning visiting the town of Matera - the 'sassi' cave area. This consists of houses carved out of the rock face along the side of a steep ravine. We enter one of the typical houses built into the rock, showing the difficult existence in these conditions. Our local guide gives us an interesting insight into life in Matera, both now and in the past. In fact his grandparents lived in these caves.

We also visit a cave church hewn out of the rock, featuring Byzantine frescoes with interesting histories. Their usage has evolved and adapted to the conditions over the years.

Since we are in the Basilicata region, our lunch here focuses on the specialties from this inland area. We spend the afternoon walking on the paths along the river valley known as the ‘gravina’. These walks will give you an even better insight into the lifestyle of times past. There are over 150 “chiese rupestre” (cave churches) in the Matera area, and the majority of them are actually strung out along this valley. You will see where the monks lived, and there are precious Byzantine frecoes in many of these churches. Historically a large proportion of the men from Matera spent most of their time living here in the valley tending their animals, and returning periodically to their families in the town of Matera.


The walks are fully guided. Distance: Morning - 3 miles / 5 km. Afternoon - 3 miles / 5 km. Duration of walking sections: 2 hrs before lunch, 3 hours after lunch. Terrain: Morning - paved, some steps and inclines. Afternoon - unsealed trails, some inclines.

Meals included: Breakfast, Lunch (3 courses including wine)

Puglia walking tour - Matera Italy

Puglia walking tour - Matera Italy

Day 6 – Locorotondo: A Bucolic Stroll

Today you walk along a scenic route through an area called the Valle d’Itria, a high plateau with an interesting mix of olive and almond trees, artichokes and capers. Your trail is an old water supply route now converted into a walking and cycling path.

Walking through this countryside you can see how some aspects of life here follow the seasonal cycles of planting and harvest, as they have done for many generations.

Locorotondo is a hilltop town in the Valle d’Itria overlooking the rich horticultural landscape. Locorotondo, has been voted as one of the “Borghi più belli d'Italia” (most beautiful villages of Italy).

The town is a great place to explore on foot as its compact centre spans a central piazza. The historic part of town - the centro storico - is circular with little lanes lined with historic buildings, including some impressive baroque archways.


The walk is fully guided. Total Distance: 7 miles / 11 km. Duration of walking: 3 hours. Terrain: Well formed walking track, level.

Meals included: Breakfast, Lunch (3 courses including wine)

Day 7 – Arrivederci Puglia

Today is our last day in Puglia. We organise transport for you to your departure point in Bari and bid you “buon viaggio”.

The tour finishes in Bari at 11 a.m.

Meals included: Breakfast

Puglia walking tour Locorotondo Italy

Puglia walking tour Locorotondo Italy

Puglia Walking Tour Dates 2024:

28 April - 4 May
22 -28 September

Tour Price: €2500

* Prices listed are based on twin share
* Single supplement of €300 for solo travellers

Tour Price Includes:

* All accommodation is included
* Meals as listed in the itinerary: breakfast every morning, plus a main meal each day of 3-4 courses including wine
* All costs/entry fees for activities listed in the itinerary are included
* All transport during the tour is included
* Travel is in our minibus with a professional driver
* Guiding and support for all the walks
* 'Italy With Pleasure' provides a tour manager for the duration of the trip on Hand to provide any assistance that you may need

Some reviews of our tours:

“Accommodation organized in Monopoli was excellent and staying in one place for 6 nights a bonus. Lunches on each walk were 5 star food and wine, also ambience. Walking ancient paths picking fresh figs off trees a delight. A small group of 6. An olive grove tour in Ostuni, a guided tour in Lecce and Matera excellent and Richie's knowledge of our walks also very informative and well delivered. He was an excellent guide. Highly recommend Italy With Pleasure. Their attention to detail and all arrangements were first class.”

“Believe all that they say in their brochure... family run, hands on and very professional. Their standards are high and they are very responsive to everyone’s needs.”

“We had an amazing trip with Riccardo (our tour guide). Ended up taking this tour for our honeymoon, and would do it over 1000x. Everything was planned to perfection. We are excited to do another one with Malcolm and his team soon!”

“I can't say enough about this tour and our guide Richie! The group was small; only 6 people; that made the tour so special and personal. everything was handled beautifully, our accommodations were very comfortable, typically Italian and very charming; the meals were fantastic; you could tell the restaurants were chosen by Italy With Pleasure with great care. a shout out also needs to go to our driver, Franco. I would definitely go on another tour with Italy With Pleasure!”

“Malcolm and Antonella are excellent tour guides, and all the dining and wine tasting they arranged on this trip were fantastic. They are very knowledgeable about the local area and had great advice on some side trips. The hotels chosen were well located and locally run. I had a wonderful time!”

“We had a fantastic time on this trip. Ricardo was wonderful and we all really enjoyed his company and knowledge of the area. Another fantastic Italy with Pleasure trip. I love this company for providing a small, private tour atmosphere, with attention to detail on food, logistics and educational site visits. You guys are amazing. Until next time.... thanks so much.”

“We had a most wonderful time and a most wonderful tour guide, Mark. Mark was personable, knowledgeable and accommodating. We would love him as our guide on another tour. Each town we visited had another guide specific to the that history and culture. Everything was beautifully planned out and well executed. Our room was beautiful, our view was breathtaking, we could not have asked for a more memorable trip!!”

See these and other reviews on Google Reviews, TripAdvisor and other review sites.

Puglia Map

Southern Italy Puglia Walking tour map

Southern Italy Puglia Walking tour photos