The Thinking Traveller

06/10/2026

We’re thrilled to have been named Best Villa Rental Company in the World for the 11th time at Condé Nast Traveller’s Readers’ Choice Awards.

A heartfelt thank you to everyone who voted for us, and to our owners, partners and teams across the Mediterranean who make what we do possible.

For almost 25 years, we’ve believed that exceptional villas, thoughtful service and deep local knowledge can turn a holiday into a lifelong memory. This award is a wonderful recognition of that belief, and of the people who bring it to life every day.

From all of us at The Thinking Traveller: Grazie mille! Σας ευχαριστώ! Merci beaucoup! Thank you!

04/10/2026

Moments to slow down, take a breath, and truly relax...

1 - Adina, Skopelos
2 - Xasteria, Skopelos
3 - Simone, Mykonos
4 - Akrothea, Meganissi
7 - Rocca delle Tre Contrade, Sicily
9 - Mythos, Kefalonia

30/09/2026

Life moves fast, time is precious, and sometimes it’s good to slow down, savour the moment, and properly celebrate what truly matters.

When these moments come along, there is no more perfect backdrop in which to raise a glass than our generously spacious, fully serviced villas. Whether it’s a milestone birthday, a special anniversary, a family reunion, a gathering of friends, or simply a getaway for the holidays, there is no more perfect backdrop to make your celebration unforgettable.

Discover our villas for extraordinary celebrations, at the link in bio.

28/09/2026

Meet Chiara, one of the incredible Local Specialists in our Puglian team.

Born and raised in Lecce, Chiara has been sharing her passion for Puglia with our guests for the past three years. For Chiara, a trip to Puglia or the Salento wouldn’t be complete without watching the sunrise at the Faro di Punta Palascìa, seeing the sunset from the ancient walls of Gallipoli, and admiring the ornate Basilica di Santa Croce in Lecce. She also considers the beautiful coastal town of Otranto a must for anyone visiting Puglia.

When it comes to food, Chiara believes everyone should try traditional Puglian sagne with tomato sauce: fresh pasta, twisted into ribbons and served with a rich, fresh tomato sauce. But for Chiara, her favourite will always be her grandmother’s and mother’s recipe.

To begin planning your own Puglian escape, head to the link in our bio.

26/09/2026

Summer in Sicily 🌞

From dramatic coastlines and secluded coves to golden beaches and ancient towns, Sicily offers a captivating mix of natural beauty, culture and Mediterranean charm. Spend long, unhurried days by the sea, discover centuries of history and savour the island’s distinctive way of life, all from the privacy of your own villa.

Let us know in the comments if Sicily is on your travel list for summer 2027.

15/09/2026

Vela, Sicily | New to our Collection

Occupying an enviable position on one of Sicily's most alluring stretches of coastline, Vela offers that magical mix of pool and garden-gate sea access that so many desire. Clean-lined, refined interiors spill out onto restful terraces, enchanting views are ever-present, and the gently buzzing, historic hamlet of Scopello is close by.

10 Guests | 5 Bedrooms | 5 Bathrooms

Head to the link below to discover Vela, and be one of the first to secure a stay in this refined villa in 2027.

https://www.thethinkingtraveller.com/italy/sicily/villas/villa-vela

11/09/2026

Discover The Thinking Traveller’s Villa Matchmaker Quiz...

Answer a few quick questions, and we’ll match you with stunning villas that fit your style, group, and expectations... no endless browsing required.

Head to the link in our bio to complete the Villa Matchmaker Quiz and discover the perfect villa for you.

Let us know in the comments which villa you were matched with!

09/09/2026

Twice a year, the fashion world turns its attention to the runways of New York, London, Milan and Paris. Yet long before a collection reaches the catwalk, inspiration often begins elsewhere. Time and again, designers, photographers and creative directors return to the Mediterranean, drawn by its extraordinary light, centuries-old craftsmanship, dramatic landscapes and architectural beauty.

From Sicily’s gilded palazzi to the sculptural whitewashed villages of Greece, these destinations have shaped everything from haute couture collections to global advertising campaigns.

Head to the link in bio to discover the places that continue to inspire the world’s most celebrated fashion houses, and the villas that allow you to experience them for yourself.

1, 5 + 9: Essence, Zakynthos
2: Pherenike, Hydra
3: Trullo Melograno, Puglia
4: Masseria Palaci, Puglia
6: Montekore, Puglia
7: Koralli, Porto Heli
8: Villa Cacciarella, Tuscany
10: Masseria Gargallo, Sicily

07/09/2026