This walking trip starts in Alberobello, a town almost entirely formed of trulli, fairytale-like dwellings with conical grey-stone roofs. The origin of these UNESCO-protected limestone houses is obscure; however, local farmers claim they were originally built to evade taxes. When the tax inspectors were nearby, the dry-stone walls could easily be dismantled by removing the keystone above the door, and quickly rebuilt after the inspection.

Starting at the hotel, we have an aperitif upon arrival before a group dinner, where we can get to know each other a little better.

Accommodation: Hotel Ramapendula (or similar)

This walking trip starts in Alberobello, a town almost entirely formed of trulli, fairytale-like dwellings with conical grey-stone roofs. The origin of these UNESCO-protected limestone houses is obscure; however, local farmers claim they were originally built to evade taxes. When the tax inspectors were nearby, the dry-stone walls could easily be dismantled by removing the keystone above the door, and quickly rebuilt after the inspection.

Starting at the hotel, we have an aperitif upon arrival before a group dinner, where we can get to know each other a little better.

Accommodation: Hotel Ramapendula (or similar)

We start with a walk to Locorotondo. Sitting on a hilltop, our destination is among the most beautiful villages in Italy and renowned for the white wine produced at Cantina Sociale, the local winery.

Following narrow country lanes, we walk over the Itria Valley hills, which are dotted with olive trees, vineyards and trulli. Once in Locorotondo, enjoy free time to explore – the Church of San Giorgio Martire, in the heart of the historic centre, is a masterpiece of Apulian baroque.

At the end of the day, we take a short train or bus ride back to Alberobello.

Accommodation: Hotel Ramapendula (or similar)

In the morning, we take a private transfer to the whitewashed hilltop city of Ostuni. After free time, in which you can visit viewpoints and centuries-old churches, we explore the surrounding countryside on foot, walking through ancient olive groves and vineyards overlooking the Adriatic.

Along the way, we stop at Agnano Archaeological Park, where we walk a winding path to see church ruins and the bones of a lady within a cave. This evening, we have a delicious dinner and stay either in a beautiful masseria – a renovated farmhouse typical of the Apulian region – or in a three-star hotel in the historic centre of Ostuni.

Accommodation: Masseria Morrone or Hotel La Terra (or similar)

Today is free to discover the many jewels of this beautiful region. We recommend a day trip to the beautiful baroque city of Lecce, known as the Florence of the South, and home to more than 40 churches and countless palaces, plus a Roman amphitheatre.

Alternatively, travel to Bari to explore the historic centre. Aside from the many beautiful old buildings, it is home to the Strada delle Orecchiette, where you can see local women create and sell the ear-shaped pasta, orecchiette.

Both destinations are reachable by train from Ostuni. In the evening, we regroup for a delicious dinner.

Accommodation: Masseria Morrone or Hotel La Terra (or similar)

This morning, we take the train to the stylish seaside town of Polignano a Mare, which is raised above the Adriatic on a limestone cliff. We first walk along the coast for beautiful sea views before exploring the historic centre, where alleys wind among white houses and lead to terraces with more views over the Adriatic.

In the afternoon, we transfer to the cave town of Matera, which is thought to have been inhabited for around 10,000 years, making it one of the oldest towns in the world. James Bond fans may recognise it as the scenic background for a thrilling car chase in No Time to Die (2021), while scenes for Wonder Woman (2017) and The Passion of the Christ (2004) were also shot here.

Its crumbling beauty is undoubtedly a lure for film directors and location scouts, but it’s the ancient Sassi districts, formed of ancient cave dwellings dug into the limestone, that are the true star here. Our hotel is in the middle of the sassi; after check-in, we enjoy our first glimpse of the enchanting alleys and unique architecture of this troglodyte town.

Accommodation: Hotel Sassi or Fra I Sassi Residence (or similar)

Today we explore Matera and further afield, walking sections of the Cammino Materano – a hiking trail linking Matera and Brindisi. After a hearty breakfast, we set off from our hotel and cross two of the Sassi’s historic quarters: the Civita, dominated by the duomo (cathedral), and the Caveoso with its caves. We head towards the ridge of Matera’s ravine and continue along a route characterised by Mediterranean scrub and cave complexes dating to the 11th century. We continue the walk surrounded by olive groves and arable land until we reach Serra Pizzuta forest. We return by public bus to our hotel.

Accommodation: Hotel Sassi or Fra I Sassi Residence (or similar)

Today we enjoy a short hike to the Murgia plateau, a vast protected area home to more than 150 Rupestrian churches dating to the eighth century, adorned with Byzantine frescoes and once inhabited by hermits. We hike to the top of the ravine, following a pathway that ends with a spectacular view of the Sassi district. In the afternoon, we walk back to Matera for a guided tour.

Accompanied by a knowledgeable local guide, we wander the narrow alleys of the cave-dwelling district and learn about the history of this fascinating place. Back in Matera, we enjoy a delicious produce and wine tasting in the historic centre and the rest of the day is free to discover the city independently.

Accommodation: Hotel Sassi or Fra I Sassi Residence (or similar)

The trip ends in Matera after breakfast. If you’d like to explore this wonderful destination a little longer, speak to your sales representative about extending your stay.