Puglia & Matera: Urban charms & rural delights

Your flight begins with included airport lounge access before flying to Bari, the bustling capital of Puglia. On arrival, collect your hire car and take to the road, driving inland and crossing over into the region of Basilicata, setting your sights on Matera. This ancient city is renowned for its ‘Sassi’ cave dwellings carved into the hillside, which have been a designated UNESCO World Heritage site since 1993. You’ll be staying right in the historic centre at a hotel which has converted 18 beautifully restored caves into unique, deeply atmospheric guest rooms with original exposed stone walls. Later on, once you’ve settled into your accommodation, you’ll head out for a guided walking tour of the Park of the Rupestrian Churches and the Sassi – a particularly magnificent sight when illuminated at sunset. 

Start your morning with a delicious, typically Southern Italian breakfast served in a 13th-century cave church, featuring the likes of Matera bread, homemade cakes and pastries, fruit, yoghurt and ricotta and mozzarella cheeses. You’ll have plenty of time to explore the mazey alleyways of Matera in more depth at your own pace today, perhaps checking out famous filming locations such as those featured in the James Bond movie, No Time to Die. There will also be a guided food-themed tour, in which you’ll get to taste an array of regional delicacies along the way, such as wines, liqueurs, cheeses and baked goods, while learning about their origins and importance to the area’s culinary heritage. 

The next leg of your road trip takes you back into Puglia to the town of Alberobello, home to the iconic ‘trulli’ houses with white bases and conical stone roofs – among the region’s most distinctive sights. Like Matera, they are also designated as a UNESCO World Heritage site. You’ll learn all about their history and how they’re built on a guided walking tour, particularly focused around the charming Rione Aia Piccola neighborhood, with ample photo opportunities as you go. Spend the night at a stylish, modern hotel just a short stroll outside the town’s historic core. Come nightfall, you may be tempted to venture back into the centre for an authentic Puglian dinner among the atmospheric surroundings of the trulli. 

Stay: Grand Hotel Olimpo

It’s just a short drive today from Alberobello to Fasano, where you’ll be spending the next three nights of your trip. Often overlooked in favour of more famous destinations throughout the region, this historic town, set where the hills and plains of Puglia’s interior slope down towards the Adriatic Sea, is an understated gem. Your luxury boutique hotel is located on the coast, around a 10-minute drive from the town centre, featuring a gorgeous outdoor pool, a spa, and direct access to the sea. It’s a blissfully serene environment to unwind and embrace a slower pace of life – but there’s plenty of scope for exploration as well as relaxation here. You may, for instance, be tempted to join a fishing tour from Monopoli, an olive oil tasting session at a local masseria, or an orecchiette pasta-making workshop, all of which will give you a deeper appreciation of Puglia’s culinary landscape. Of course, it’s also worth taking the time to explore Fasano’s delightful whitewashed centre. 

Today you’ll set off towards the south, travelling down the heel of Italy’s boot to Lecce, nicknamed ‘the Florence of the South’ due to its abundance of baroque architectural masterpieces. Wandering between its honey-hued streets and elegant piazzas feels like taking a step back in time, with an array of ornate landmarks to marvel at, including Lecce Cathedral, the Roman Amphitheatre and the Basilica di Santa Croce. While exploring, be sure to seek out a sumptuous pasticciotto – a custard-filled pastry originating from Lecce that goes perfectly with a coffee. You’ll also have the chance to visit a traditional masseria in the nearby countryside for a guided tour and an organic cheese tasting session. Your hotel for these two nights is set within a 19th-century mansion right in the heart of Lecce, so you’ll be perfectly placed for making the most of the city’s plethora of fabulous bars and restaurants. 

The final leg of your Puglian adventure brings you to Otranto, Italy’s easternmost town. It’s home to an imposing 15th-century Aragonese Castle, built to protect the city from attacks from the Ottoman Empire, as well as an 11th-century Norman cathedral with an enormous floor mosaic. You’ll learn all about the city’s fascinating history and its strategic importance over the centuries on a guided walking tour. There are some gorgeous swimming spots and hiking trails along the coastline around Otranto, too, from which it’s possible to see the mountains of Albania on the horizon on a clear day. Your base for these last two nights is just outside the town, tucked away in a peaceful, rural spot among olive groves and luscious Mediterranean gardens. 

Make your way to Brindisi Airport this morning, where you’ll drop off your hire car before catching your flight home.