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Walking in the Heel of the Italian boot
Lecce-Otranto-Gagliano del Capo-Gallipoli-Porto selvaggio-Nardò-Galatone
If you dream of exploring southern Italy at a slow and authentic pace, walking holiday in PUGLIA are the perfect way to experience its charm. The Salento Peninsula — the southernmost province of Apulia — forms the “heel” of Italy’s famous boot and is one of the most captivating corners of the Mediterranean. Surrounded by the Adriatic and Ionian Seas, Salento offers a landscape of olive groves, whitewashed villages, and endless coastline, where history, culture, and cuisine blend seamlessly.
Over the centuries, this land has been home to many civilizations — from the Messapians and Greeks to the Romans and Normans — each leaving behind architectural treasures, language traces, and culinary traditions. During the Middle Ages, Salento was frequently attacked by Saracen pirates, prompting the construction of numerous coastal watchtowers. Many of these towers, dating from the 15th and 16th centuries, still guard the shoreline today, offering spectacular sea views along your walking routes.
Salento is famous worldwide for its Mediterranean cuisine, crystal-clear sea, and the lively rhythm of its folk music, the Pizzica — a traditional dance that embodies the soul and energy of this region.
Your walking holiday in Puglia begins in Lecce, the “Florence of the South.” This elegant Baroque city captivates visitors with its ornate churches, palaces, and Roman amphitheatre. Stroll through the narrow streets built from golden sandstone, discover hidden piazzas, and enjoy lunch in a cozy trattoria or stylish wine bar. Local dishes such as cecamariti — pancakes made with zucchini, tomatoes, onions, and chili — and puccia, a delicious sandwich filled with cured meats, cheeses, and vegetables in oil, will give you a true taste of Apulian tradition.
Your journey continues to Otranto, a picturesque seaside town and former Roman harbor. Here, you can explore the impressive Aragonese Castle, admire the stunning mosaic floor in the Romanesque Cathedral, and relax in one of the many seafood restaurants overlooking the harbor.
Each stage of your Puglia walking tour reveals something new — from ancient Byzantine crypts and prehistoric sites to peaceful rural paths lined with dry-stone walls and centuries-old olive trees. Local train connections make it easy to reach authentic villages and hidden corners of the region, allowing you to experience a side of Puglia rarely seen by tourists.
Whether you’re drawn by the history, the cuisine, or the beauty of the Mediterranean landscapes, a walking holiday in Puglia’s Salento region offers the perfect blend of adventure, relaxation, and cultural discovery. Step by step, you’ll uncover the heart of southern Italy — a land where time slows down, the food tastes of sunshine, and every path tells a story.
The daily program of the 8-day tour
Arrival in Bari/Brindisi and you go by bus, train or with booked transfer to Lecce. In the late afternoon, briefing about your trip (English). Then you have time to do a short walking tour in the old town of Lecce, the Florence of the South. You will fall in love with its Spanish baroque style and its Roman remains.
Overnight in Lecce
Transfer by train from Lecce to Giurdignano. You walk through fields, beautiful olive groves and reach Giurdignano, where you will visit the megalithic garden with its dolmen and menhirs of the Bronze Age. Then you will head to Casamassella where you will admire the ancient looms brought back into production by the “Le Costantine” Foundation. Walking through the Idro Valley, you will discover an ancient Byzantine crypt. At the end of today’s stretch, you will reach Otranto, the pearl of the Adriatic, with its Cathedral and its medieval “tree of life” mosaic floor.
Overnight in Otranto.
Distance: 14 km / 8,7 miles; Walking times: 4 hours: total Ascent:+ 72m
Today you will explore the natural wonders of the surroundings of Otranto, like the Bay of Orte, then the lighthouse of Punta Palascia and the Bauxite Quarry. Today you will start from the castle of Otranto and go through the Porta a Mare. Once you have reached the main pier, you walk further along the coast towards the Snake Tower, which can be easily reached following easy trails.
You will see imposing cliffs and caves with stalactites and stalagmites. Finally, you will reach the Lighthouse of Punta Palascia and then a bauxite quarry, whose intense colours create a unique landscape. From the cave, you go back to Otranto where you will have your overnight stay.
Overnight in Otranto.
Distance: 16 km / 9,9 miles; Walking times: 4,5 hours; total ascent 182m
In the morning, you take the train from Otranto to Gagliano del Capo (travel time 1 hour and 10 minutes).
You will reach your accommodation and then get ready to walk along the trail called Ciolo, which goes down towards a canal. The footpath will offer amazing views. Once you have reached the Ciolo bridge, take the foothpath of the Cipolliane, which starts right there. The vegetation is particularly interesting (agaves, capers, prickly pears etc.). You will visit the caves of the Cipolliane (with stalactites and columns, galleries and fossils and bird colonies). Back on the trail, you continue to Novaglie, where you can take a break) or go back to the Ciolo Bridge if you like to swim. After passing a reproduction of the Madonna di Leuca, you continue to Gagliano.
Overnight in Gagliano del Capo.
Distance: 13 km / 8 miles; walking time: 4 hours; total ascent: + 192m
This day is dedicated to the discovery of the Cape of Leuca, the southernmost point of Apulia, and of the beautiful town of Gallipoli. First, you will cross ancient paths that connect small villages: the first stop is Patù with its Centopietre, an enigmatic monument created with a funerary function and coming from Vereto, an ancient pre-romanic city situated in the vicinity. In Giuliano you will visit the Church of San Pietro and the castle; in Barbarano you will visit the Sanctuary of Leuca Piccola and its hypogeum, an ancient destination for pilgrims and a stop for the faithful people of Leuca. From the station of Ruggiano-Salve, you take the train to Gallipoli (travelling time 1,5 hour) You have time to visit the old city of Gallipoli. From here you take the train to Gallipoli. You will visit the historic centre, surrounded by the sea and you will get a chance to taste a drink on a terrace with stunning views. Situated on an island, this little fishermen village is surprising for its light, its alleys and its fish market.
Overnight in Gallipoli
Distance: 9 km / 5,6 miles;
Walking times: 3 hours; Total Ascent: +42m
After breakfast, a short train transfer (30 min.) to reach Nardò.
From Nardò you walk along the ancient dry stonewalls and amongst olive groves. You will arrive at the bottom of the slope of the Alto promontory where, on the upper plateau, you will find the Tower of Santa Maria dell’Alto, whose construction dates back to 1568. Then you will move down to Porto Selvaggio, which became a regional natural park in 2006: in the area, there are numerous karstic caves with the remains of communities dating back to the Palaeolithic era. Then you will reach the tower of Uluzzo. The itinerary ends in Santa Caterina where its numerous ice cream shops await you. From here, a private transfer will take you back to Gallipoli.
Transfer from Santa Caterina to Gallipoli
Overnight with breakfast in Gallipoli
Distance: 17 km / 10,5 miles
Walking times: 5 hours
Total ascent: + 110m
From Gallipoli you will go to Galatina by train and visit the historic centre with the magnificent basilica of St. Catherine of Alexandria. Then, still by train, you will reach Lecce. Here you will have time enough to visit the city, also called “the Florence of the South”. You will see Baroque palaces, courts but also a Roman theatre and amphitheater, Santa Maria della Croce, the Cathedral etc.
Overnight with breakfast in Lecce
After breakfast ends your walking tour through Salento
Walking in Salento
Lecce-Otranto-Gagliano del Capo-Gallipoli-Porto selvaggio-Nardò-Galatone
LEVEL 1,5
Easy, tour for all. Some walking experience needed but particular training are not requested for this tour. Not too many differences of level, almost all walking on very easy terrain. The area is mostly flat, so you will encounter very few ascents. You will walk along secondary roads and walking paths: 50% asphalted and 50% on gravel. Walks between 3 to 5 hours
Average daily distances:
9 km / 5,6 mi – 17km / 10,5 mi
Total km:
Total 69 km / 42,8 mi
DEPARTURES:
Every Friday and Saturday from 07/01 until 18/07 (last departure) and from 28/08 till 21/12/2026 (last departure). Start on other days possible paying a supplement (€ 100 p.p.)
PARTICIPANTS:
Minimum 2 (solo travellers upon request)
START / FINISH:
Lecce / Lecce
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