Italy With Pleasure

Puglia Walking Tour

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7 Day Tour
14 people max
All inclusive
Min Age : Refundable deposits

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 culture – it opens up a whole side of Puglia that most people never see. The walks are generally a half day duration and of moderate intensity.

Our tours are a balance between being informative (examples of the culture and lifestyle, historical details) as well as having everything that makes for an enjoyable trip (long lunches in good restaurants, a relaxed pace). We plan the itinerary in the way that you would plan to travel yourself, or with a group of friends.


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.



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.

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



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.



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!)



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.



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.



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.

Puglia Walking Tour Dates 2024
Puglia Walking Tour Dates 2025
Cost and Inclusions


* Price is denominated in Euros. Price listed is based on twin share
* Single supplement of €300 for solo travellers



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

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.


A R, AUSTRALIA Google Reviews Logo

Puglia Walking Tour. September 2019
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. The walking was easy. As a couple we would perhaps have liked a little more of a challenge. Highly recommend ItalyforPleasure. Their attention to detail and all arrangements were first class.

P B, CANADA Google Reviews Logo

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.

C L, USA Google Reviews Logo

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.

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