








Italy: Puglia
Average customer rating 4.8 / 5(17 verified reviews)
Explore Puglia’s pristine coastline, accompanied by glittering sea vistas, fragrant wild flowers and the gentle murmur of ocean waves as you head from Lecce towards Puglia’s most southerly point at Santa Maria di Leuca. The region boasts a variety of wonders, from the Baroque buildings in Lecce and the Romanesque cathedral in Otranto to natural phenomena like the lunar landscape of the Blue Lake and the dramatic Zinzulusa Cave with its extensive stalactites and stalagmites.
Our air prices include standard flights and transfers.
We can book connecting Eurostar services from London and Ashford if you prefer not to fly.


Admire the city’s superb Baroque architecture before dinner.
You stay at B&B la Bella Lecce

Lecce
Run by an Italian-English couple, Roberto and Stephanie can provide you with essential local information to ensure you make the most of your stay in Lecce. Situated within Lecce’s historic city walls, this small but pretty B&B is located within a late 19th century building with traditional vaulted ceilings and golden stone walls.
All rooms feature free Wi-Fi, television, A/C and private bathroom.

We take you to the sandy shores of Torre dell’Orso, from where you set off along a low clifftop path with views over the Faraglioni di Sant’Andrea, lofty sea stacks that have seemingly fallen from nowhere into the azure waters. Head through pine trees and the golden sands of Baia dei Turchi before arriving in spectacular Otranto.
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You stay at HOTEL ALBANIA

OTRANTO
This aptly named hotel takes its name from the majestic Albanian mountains which on a clear day are visible from the hotel’s panoramic dining terrace. Located in the centre of Otranto, it’s ideally situated for exploring the Old Town, whilst being just a short walk from the seafront and the town’s public gardens.
All rooms are furnished with a simple yet bright decor and include Wi-Fi, television, A/C, private bathroom with WC and shower, minibar and safe.

There’s time to explore Otranto and its Romanesque cathedral, home to the famous ‘tree of life’ mosaic, then a glorious coastal path takes you past the stunning lunar landscape of the Blue Lake en route to Italy’s easternmost tip, from where you can see as far as Albania on a clear day! End the day in the small village of Uggiano La Chiesa.
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You stay at MASSERIA GATTAMORA

UGGIANO LA CHIESA
The masseria – a traditional fortified farmhouse – dates back to 1763 and has been transformed into a small but cosy hotel, with the former oil mill and hay store now housing the bedrooms, and the restaurant in the former stables. Facilities include an outdoor pool, gardens, bar and the beautiful restaurant, which comes with vaulted ceilings and open fireplace.
All room are comfortable, spacious and tastefully decorated with exposed white walls and high vaulted stone ceilings.

Wild flowers and sea views abound on today’s walk as you follow the coastal path skirting the Sant’Emiliano promontory, topped by its panoramic 16th century lookout tower – built to protect the area from marauding pirates! The azure seas blend with impossibly blue skies as you continue to Porto Badisco – the perfect stop for a scenic lunch – before a gentle walk with more far reaching views takes you to the thermal resort of Santa Cesarea.
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You stay at VILLA CESAREA

SANTA CESAREA TERME
Villa Cesarea is located in the centre of Santa Cesarea Terme, overlooking the sea. The residence dates back to the early 1900s and was lovingly restored in 2018, retaining many of its charming original features. There is a lovely garden surrounding the villa with several terraces where you can sit back and relax.

A shorter walk today with a background of lush hills and glittering waters, to the exceptionally beautiful town of Castro. Relax on its sunny terraces, bathe in the sea, visit the archaeological museum or the phenomenal Zinzulusa Cave – so called for the stalactites that seemingly hang like rags (zinzuli) from the cave ceiling. There is so much here to enjoy.
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You stay at HOTEL DEGLI ULIVI

CASTRO
Just a 10-minute walk from the beach, the family run Hotel Degli Ulivi boasts superb sea views, with its balconies overlooking the sparkling Mediterranean. Rooms are simply furnished but comfortable, with ensuite facilities and sea view. The hotel also has a bar and restaurant which serves both Puglian and traditional Italian dishes.

Follow a coastal trail, fragrant with wild herbs, to the beautiful inlet of Acquaviva, with its pretty beach and picturesque marina. Then it’s truly outstanding walking along age old trails boasting superb sea vistas, accompanied by the murmur of ocean waves, before heading inland to Tricase with its narrow winding alleyways and magnificent central piazza.
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You stay at B&B ROSA DEI VENTI

TRICASE
Located in the quiet and historic centre of Tricase, this charming B&B offers a traditional feel with modern amenities. There are just 3 rooms, all well equipped for a comfortable stay, with tiled floors, exposed honey coloured stone ceilings and whitewashed walls. There is also an internal courtyard area where breakfast is taken.

After a short transfer to the pretty harbour at Novaglie, a spectacular clifftop trail winds its way through a breathtaking landscape of rocky cliffs dotted with euphorbia and prickly pear, with stunning views over the coastline and azure waters beyond. Today’s final stretch runs along the Via Francigena del Sud, as you follow in the steps of pilgrims en route to the Holy Land to the Sanctuary at Santa Maria di Leuca.
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You stay at HOTEL TERMINAL

SANTA MARIA DI LEUCA
The Hotel Terminal has a prime location on the sea front, with lovely views over to the Punta Ristola Leuca, the southernmost point of Italy’s ‘heel’. Rooms at the Hotel Terminal are comfortable and well equipped whilst other facilities at the hotel include a restaurant, bar, outdoor pool and sun terrace. The hotel also benefits from its own private beach.

12.0
Kg CO₂e
per person, per night
Relative to other Headwater trips
We measure emissions from the parts of the holiday we organise — including accommodation, in-trip transport, meals and activities — and express them as CO₂e per person, per night. Our label doesn’t include your travel to and from the start of the trip. As a Certified B Corp, Headwater is committed to reducing this figure and to positively impacting local communities, the local environment and our staff. Learn more