The Thinking Traveller

Private villa rentals in the Mediterranean

By Patrick Janelle

During the summer of 2018, over coffee in London, I met Rossella Beaugié, the stylish owner of The Thinking Traveller, a collection of homes sprinkled across Sicily, southern Italy, and a handful of Greek islands.

Rossella and her husband, Huw, founded the company in 2002 when they noticed many of their Italian friends (Rosella herself is a native of Sicily) had gorgeous vacation properties that were sitting empty most of the year. What was once a loose collection of properties is now a tightly curated hospitality brand, akin to an upscale Airbnb. The difference is that The Thinking Traveller, rather than developing a gigantic database of properties, focuses on high-touch service and selecting thoughtful locations, which range from smaller, four person homes to giant villas that accomodate dozens of guests. Nearly all properties have views of oceans, cliffs, or vineyards, and most have pools.

Hospitality plays a key role: leading up to the trip, upon arrival at the airport, and during the guests’ stay, a member of the extended team is just a text away. Housekeeping service, along with breakfast preparation each morning, is included, and the company offers add-on services like an in-villa chef or booking guides for tours of the area.

In October 2018, drawn to Sicily’s food and wine culture, my friends and I opted to stay at La Prora, a sprawling property at the foot of one of Sicily’s most beautiful—even if touristy—towns, Taormina. There are five bedrooms, six baths, two living rooms, a large chef’s kitchen, four patios, and two additional freestanding units, each with a small living room and kitchenette. The property—once a pizza restaurant—is now the vacation home to a Norwegian family. And for the week, it was ours, too.