The Thinking Traveller

04/06/2026

In August, the sun-drenched landscapes of the Valle d'Itria are at their most alluring, with ancient olive groves, whitewashed Trulli, and incredible Masseria, all tempered by a gentle breeze that drifts through the valley and brings welcome relief from the heat.

This is a season of extraordinary abundance, when fragrant peaches, sun-ripened tomatoes and just-picked produce from local markets elevate every meal, enjoyed in the privacy of your villa.

Discover our full collection of villas in the Valle d'Itria, at the link below.

1-2: Montaltini
3-4: Trullo Pinnacolo
5-6: Casina Cinquepozzi
7-8: Masseria Donnagnora
9-10: Masseria Palmieri

https://www.thethinkingtraveller.com/results?subRegions=valle-ditria&page=1

03/06/2026

La Rona is a charming and meticulously restored Masseria nestled in the heart of Puglia’s picturesque Valle d’Itria. Perched on a hilltop, the villa offers breathtaking panoramic views and unforgettable sunsets. There is even a special observation area just for enjoying these magical moments with sundowners.

Discover La Rona at the link in bio.

02/06/2026

This October, whether you’re planning a half-term escape, fall break or a long holiday weekend, there’s never been a better time to slow down and reconnect with family in the Mediterranean. The sea remains warm, the pace gentler, and the summer crowds have long since faded away.⁠
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Our handpicked villas in Italy, Greece and France offer the freedom, privacy and space to experience travel at your own rhythm. What’s more, our villa specialists can tailor offers depending on your group size and length of stay.⁠
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Take the first step in creating your next memories with us, at the link in bio.

30/05/2026

Relax in the Mediterranean in one of our luxury villas with a private chef included, where you'll never have to lift a finger.

A discreet team of staff will keep your home-from-home spotless, and a private villa cook will prepare delicious, authentic meals in the local cuisine for you. All of which means that you can spend every moment of your catered holiday doing the things you love with the people you love.

Discover the full range of villas with chefs included, at the link below.

https://www.thethinkingtraveller.com/collections/villas-with-cook-included

28/05/2026

📍Arbolì, Villasmundo, Sicily

Hidden away on the historic 150-acre San Giuliano estate between Catania and Syracuse, Arbolí is an irresistible four-bedroom villa for anyone in search of privacy, peace and the restful rhythms of life in the country.

With views across infinite orange orchards to Mount Etna, and a timeless sense of place, this soulful 200-year-old home subtly combines original architectural features with all the 21st-century comforts you'll need for a carefree escape.

Discover more at the link below.

https://www.thethinkingtraveller.com/italy/sicily/villas/arboli

28/05/2026

📍Arbolì, Villasmundo, Sicily

Hidden away on the historic 150-acre San Giuliano estate between Catania and Syracuse, Arbolí is an irresistible four-bedroom villa for anyone in search of privacy, peace and the restful rhythms of life in the country.

With views across infinite orange orchards to Mount Etna, and a timeless sense of place, this soulful 200-year-old home subtly combines original architectural features with all the 21st-century comforts you'll need for a carefree escape.

Discover more at the link below.

Book Arbolì, a 4-bedroom villa for up to 8 guests with The Thinking Traveller. Named the World's Best Villa Rental Company by Condé Nast Traveller.

23/05/2026

Escape to Torre di Fonterinaldi in the Tuscan countryside for a truly undisturbed retreat...

14 Guests | 7 Bedrooms | 6 Bathrooms

Discover our full range of Tuscan villas at the link below.

https://www.thethinkingtraveller.com/italy/tuscany/villas/torre-di-fonterinaldi

23/05/2026

Picture this: complete privacy, idyllic surroundings, and the cleaning and cooking handled discreetly in the background.

Our handpicked collection of serviced villas allows you to enjoy tailored support such as daily housekeeping, private chefs and local concierge specialist assistance. So your focus remains exactly where it should be, on unwinding.

1-2: Pacifica, Meganissi
3-4: Masseria Palaci, Puglia
5-6: Casetta Firenze, Tuscany
7-8: Palazzo Musmeci, Sicily
9-10: Salinedda Six, Sardinia

Discover the full collection of serviced villas, at the link below.

https://www.thethinkingtraveller.com/results?amenities=68&page=1

18/05/2026

Discover more than just a place to stay, step into a villa where relaxing mornings melt into serendipitous afternoons, where laughter lingers, and where every moment feels entirely your own. Unlike the shared rhythms of a hotel, a villa offers the luxury of space, privacy, and unhurried freedom: no schedules to follow, no crowds to navigate, only the gentle cadence of your own making.

It is this sense of effortless living that transforms a villa stay into something deeper, a place where time slows, connections flourish, and memories are shaped to last long after the journey ends.

Discover our full collection of villas at the link below.

https://www.thethinkingtraveller.com/results

08/05/2026

The Perks of Being Early...

In a world where travel costs continue to climb, locking in next year’s escape at this year’s rates is a rare opportunity. Whether you’re drawn back to a long-loved favourite or considering somewhere new, booking early brings greater choice, added reassurance, and time to shape every detail.

To secure your 2027 stay at 2026 prices, you’ll need to book by 30th June. Our villas are exclusively available through us, so you can check live availability and book online, 24/7, whenever it suits.

Head to the link in our bio to discover our collection of villas available for 2027 - at 2026 prices.