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Gold Standard Stays

Bringing high-end design and thoughtful service to top Mediterranean destinations, the Thinking Traveller is the insider’s choice for Europe’s most remarkable villas

Greece
Sponsored by

Created for travellers who believe that where you stay matters as much as your destination, The Thinking Traveller has quietly set a new benchmark for Mediterranean villa holidays. Voted Best Villa Rental Company in the World ten times by Condé Nast Traveller for its locations across Sicily, Puglia, Tuscany, Greece and Corsica, the company has built an unrivalled reputation over its two decades of operation.

 

 

Each villa is personally inspected and rigorously selected. These are homes shaped by their owners to be nothing short of extraordinary, chosen for their architecture, design, location, setting and atmosphere. The portfolio spans a rich range of styles and histories, and each property has an individual story to tell. Only those imbued with heart, soul and an inimitable sense of local magic make it into The Thinking Traveller family.

 

From tastefully converted stone castles in Sicily and elegant Tuscan farmhouses to sleek, contemporary villas in the Greek islands, magnificent homes in the Corsican mountains, and even iconic and charming trulli in Puglia: whatever the aesthetic, each home offers a genuine connection to its surroundings.

 

Sicily

Sicily

Tuscany

Tuscany

Puglia

Puglia

Corsica

Corsica

Greece

Greece

 

Every Thinking Traveller stay begins with an exceptional villa, but it is the thoughtful service behind it that really sets the brand apart. Discerning, well-travelled guests are paired with specialists who know each property intimately and take the time to understand exactly what their clients value. Working closely with dedicated local teams who live and breathe their destinations, they craft stays and itineraries that feel deeply personal, leaving guests free to focus on what really counts: time together. Whether planning a multi-generational family celebration, a romantic escape or a week of culinary immersion, the advice is carefully considered, honest and deeply knowledgeable.

For travellers who appreciate authenticity and exceptional service, The Thinking Traveller offers a refreshing alternative to traditional hotels and resorts. It’s an invitation not just to visit the Mediterranean, but to truly live it – and return home with memories that endure long after the journey ends.

Explore the collection and book your 2026 stay now.

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