City Life Magazine photographer Jesse Milns embarks on a five-day adventure with The Thinking Traveller for a picture-perfect getaway along the heel of Italy’s boot.

Puglia has a diverse landscape and an abundance of architecture that’s soaked in thousands of years of heritage. Located where the Adriatic Sea meets the Ionian, olive trees sprout from the rich red soil up to the conical stone roofs of the trulli. The southern region is still low-key in terms of tourism, which makes it ideal for those wanting to experience a quieter vacation away from the typical Italian hot spots that include Rome, Venice and Milan. My Think Puglia adventure was jam-packed with picturesque vistas, amazing food and luxury accommodations that made for an unforgettable experience. Here’s my daily rundown of things to do and see in this untapped destination:

DAY 1:Masseria Cisterna Rossa
Located in Ruffano, Masseria Cisterna Rossa is one of The Thinking Traveller’s “Think Exquisite” villas. This gorgeous stay sleeps eight in four bedrooms, has a turquoise outdoor pool, multiple common areas and daily maid service. The perfect little oasis is an easy drive to small towns like Gallipoli and Otranto, and minutes away from sandy beaches. This villa was my personal favourite because it was casually elegant — the pool area and surrounding olive grove seemed to glow at dusk, and the rooftop terrace was perfect for watching the sunset while sipping some locally produced wine.

DAY 2:Villa San Vincenzo and Gallipoli
Also a Thinking Traveller “Think Exquisite” villa, the secluded estate of Villa San Vincenzo accommodates 10 guests in five luxury-appointed bedrooms and has a 24-7 concierge on-site. The enormous garden is full of apricot and olive trees that wrap around the multiple houses on the property, which feature traditional Salento architecture and a stunning pool. Nearby is the Ionian coast town of Gallipoli, which means “beautiful city.” Its town centre is formed on a tiny island surrounded by defensive walls and accessed by a bridge. Inside those walls is a series of restaurants, churches and buildings with a fish market next to a bustling harbour.

DAY 3:Masseria Curti Vecchi and Otranto
From the outside, Masseria Curti Vecci looks like an old fortress. Inside is a huge courtyard with the villa itself wrapping around it. The stone walls keep a very rustic feel but are accented beautifully by the mix of modern and antique furniture. The kitchen is a dream for anyone that loves cooking.
Otranto is situated on Italy’s most eastern tip and is known for the “martyrs of Otranto.” The bones of the martyrs — 800 people killed by Islamic Turks over religion — are still displayed in the walls of the town’s cathedral. The cobblestone streets wind past ristoranti and heritage sites to seamlessly blend the ancient architecture and new businesses that inhabit it.

DAY 4:Santa Maria di Leuca
On the southernmost tip of Puglia is Santa Maria di Leuca, which is where you will find Villa Blanca. Inside are five bedrooms that sleep 10, as well as numerous living areas that make you feel at home as soon as you set one foot inside. The pool with a Jacuzzi corner and view of the town is breathtaking.
Some of the best seafood you can have in Italy, let alone the region, is at Ristorante Lo Scalo in Marina di Novaglie. Its view of the crystal-clear water crashing up against the rocks creates an atmosphere like no other. Fresh lobster, octopus and white anchovies are served alongside pasta, house-made bread and local seasonal vegetables.

DAY 5:Casa Romigi and Trullo Terra Dolce
West of Brindisi is Valle d’Itria, the native land of trulli (ancient round stone huts with conical roofs). These unique structures are specific to the region and can be found converted to restaurants, stores or homes.
Casa Romigi is a renovated series of trulli with four bedrooms and a beautiful pool. With huge windows on one side and sliding doors on the other, the kitchen is bright and spacious and has a beautiful dining table. This is perfect for enjoying an espresso and friselle for breakfast while watching the sunrise.
Trullo Terra Dolce is another lovely home restored from a series of trulli. It keeps the rustic feel in every room with lots of reclaimed wood furnishings and East Indian-style accents. The kitchen and wood-fired pizza oven just outside are perfect for creating authentic Italian meals.

Photographer Jesse Milns’s “Think Puglia” trip was organized by The Thinking Traveller, a villa rental company that assists and supports travellers looking for stays in luxury villas and seafront properties throughout Puglia and across the Mediterranean. For more info, visit www.thethinkingtraveller.com