About us
We’re the only keyholder to a family
of unique houses and experiences
We seek out houses, villas and estates with soul. And because we’re the only company entrusted with renting them, we know them intimately – their story, their design, their availability – so we can introduce you to your perfect place.
“Incredible hand-picked properties and locations... and the people at The Thinking Traveller making sure you have the best holiday of your life… The human experience from the moment you think of booking really became the defining reason to travel with The Thinking Traveller.”
- Sheree Commerford, CANVS Bottega
We share places close to our hearts
Created and run by locals, The Thinking Traveller believes it’s a pleasure to discover somewhere through those who know and love it. Our local experts’ knowledge of our villas and beyond – a private boat to a secret beach, dinner by a renowned chef, that festival on the hill – creates experiences that become memories.
“Able to open doors that would otherwise be locked to us, possessing an almost preternatural ability to know what we wanted for our holiday and then executing plans with ruthless precision.”
- Alex Preston, Harpers Bazaar
We introduce people to soulful
places in thoughtful ways
Passionate about human connections
We are a community united by a love of places with soul. Our success is in the enduring relationships we have built over our 20 years – with villa owners, local communities and guests. By working with people who share our passion for hospitality, we deliver impeccable service and experiences for every guest.
We share places close to our hearts
Rossella and Huw founded The Thinking Traveller in Sicily in 2002, embarking on a voyage around the Mediterranean that continues to inspire them. On their travels, they met Dimitris and Anna, who had started a business with similar values in the Greek Islands in 2008, and in 2021 the two companies joined forces. Today, the four founders lead The Thinking Traveller with an undiminished passion for their homelands and a shared belief that the best way of discovering somewhere special is through those that know and love it.
Villa Matchmaking service
Because our local experts have personally visited each of our destinations, we know exactly what makes them special. Tell us what your ultimate villa holiday looks like, and allow us take care of the rest
