The Thinking Traveller

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

02/09/2026

Join us from the 3rd to the 10th of October for an immersive culinary retreat at Rocca delle Tre Contrade, hosted by Chef Cortney Burns alongside Rocca’s own chef, Dora Maugeri, as Sicily’s autumn harvest reaches its peak.

Spend a week exploring the island’s seasonal bounty through hands-on masterclasses in fermentation, curing, candying, drying, infusing and condensing. From vineyards and olive mills to Etna’s slopes and the coast, discover how to transform Sicily’s abundance into a flavour-packed pantry that can be enjoyed long after the retreat ends.

Cortney Burns has spent her career exploring the art of preservation, combining ancient techniques with contemporary practices to unlock new layers of flavour. Her arrival in Sicily feels like a homecoming, with her affinity for the resourcefulness of island cultures naturally intersecting with culinary traditions that have shaped Sicily for millennia.

The week coincides with the release of Cortney’s new book, Cultured, a guide to culinary alchemy and a reflection of the retreat itself: reconnecting with food at its source and learning to build an abundant pantry to draw from year-round.

Using ingredients from Rocca’s fertile grounds, alongside trusted regional producers, local fishermen and natural winemakers, this retreat is an opportunity to get hands-on, learn new skills and share in the convivial spirit at the heart of Sicilian life.

Head to the link below to enquire about spaces on this exclusive culinary retreat at Rocca delle Tre Contrade.

https://www.thethinkingtraveller.com/italy/sicily/chef-cortney-burns-at-rocca-delle-tre-contrade?utm_source=facebok&utm_medium=post&utm_campaign=courtney

01/09/2026

Schools may be reopening, but our syllabus is a little different.

Our founders created The Thinking Traveller with the belief that travel offers an inspiring, hands-on and exciting way to learn – something they wanted their own children to experience. This October half-term, why not broaden young minds and spark curiosity through Mediterranean traditions, design and local knowledge? Whether taking a cooking class to make pasta from scratch, learning to paddleboard, or visiting a historical theatre, there's a world of discovery waiting beyond the classroom.

Head to the link below to begin planning your half-term retreat.

https://www.thethinkingtraveller.com/collections/last-call

27/08/2026

Join us from the 26th of September to the 3rd of October for an immersive wine and culinary retreat at Rocca delle Tre Contrade, hosted by Isabelle Legeron, Master of Wine, founder of RAW WINE, and acclaimed author of "Natural Wine: an introduction to organic & biodynamic wines made naturally".

Learn about the emerging wine areas of Sicily, enjoy exclusive access to wine makers and experience the Sicilian wine harvest first hand during this 7-day all-inclusive retreat. The retreat will feature a unique introduction to the Sicilian culinary tradition, along with dedicated wine pairings.

The culinary experience will be led by Rocca's much-loved resident chef, Dora Maugeri, whose infectious passion for Sicilian food and deep-rooted knowledge of the island's culinary traditions bring every meal to life.

Rocca delle Tre Contrade's cellar, which is filled with the owners' impressive selection of Sicilian wines, echoes with history, for the property was built in 1850 as part of a large wine-producing estate. With its sense of majesty and its commanding position atop its very own panoramic hill, it was one of the most impressive Etna wineries in its heyday.

It was painstakingly and lovingly restored to its former splendour by the current owners in 2012, and today its extensive grounds are home to evergreen citrus groves, vegetable gardens, fruit orchards, evocative terraces, and a beguiling, L-shaped infinity pool.

Head to the link below to enquire about spaces on this exciting retreat at Rocca delle Tre Contrade.

📷: 1.

https://www.thethinkingtraveller.com/italy/sicily/the-sicilian-wine-harvest-at-Rocca-delle-Tre-Contrade

25/08/2026

Oleana blends local materials with contemporary design to magical effect. Calm, warmly welcoming interiors flow outside at every opportunity, allowing guests to live an al fresco lifestyle with minimal fuss.

Discover more at the link below.

📍Kea, Greece

https://www.thethinkingtraveller.com/greece/kea/villas/oleana

23/08/2026

“The Great Butterfly of the Sea”

Favignana, at the centre of the Egadi Islands, is a hidden gem off Sicily’s western coast, offering a perfect blend of unspoiled nature, crystal-clear waters, and authentic Italian charm. With its fascinating history, rugged landscapes, secluded beaches, and some of the best seafood in the Mediterranean, Favignana is a true Italian escape.

The perfect time to visit Favignana and the Egadi archipelago is September, with warm sea temperatures, a pleasant breeze, and a thinning of the summer crowds.

Discover more about Favignana at the link in bio.

20/08/2026

From the iconic conical roofs of traditional trulli to beautifully restored masserie, Puglia's architecture is unlike anywhere else in Italy. Originally built to support the region's agricultural communities, many trulli still stand today, particularly in the old town centre of UNESCO-listed Alberobello, where their distinctive whitewashed forms have become synonymous with Puglia itself. Historic masserie and casine also reflect the region's rural heritage, but on a grander scale, and many of these former manor houses and country estates have been carefully restored for modern living.

With a spectacular coastline, exceptional cuisine, and timeless landscapes, it's a destination best experienced from the comfort of a luxurious villa.

Discover our full collection of Puglian properties at the link below.

https://www.thethinkingtraveller.com/italy/puglia