Great travel stories are rarely linear. For Rossella Beaugié, co-founder of The Thinking Traveller, her journey from academic research labs in Paris to curating some of the Mediterranean’s most covetable private villas is, as she puts it, “a bit of a life and love story.” When we speak, Beaugié is warm, thoughtful, and quietly passionate. Nearly 25 years into building The Thinking Traveller, she still lights up when talking about Sicily, about clients who have become almost like family, and about the transformative magic of shared experiences in beautiful places.

But before villas and Mediterranean sunsets entered the picture, Beaugié’s life looked very different. She and her husband (also her business partner) were living in Paris, pursuing demanding, high-achieving careers. “I was doing my PhD in biology, and my husband was doing an MBA,” she recalls. “We had our careers, our paths, everything laid out.” Then life intervened. “We lost Huw’s brother quite suddenly,” she says gently. “And that really makes you realize, ‘What do you want to do with your life?'” Soon after their wedding, the couple travelled back to Sicily—Beaugié’s homeland—for a holiday. It was a defining moment of realization. “We suddenly saw there were different ways of living our lives.” At the time, Sicily wasn’t as well known as the couple felt it deserved to be. “[People didn’t know] how amazing Sicily is, how rich it is culturally and naturally,” she explains. Her husband had the initial business idea: a more thoughtful, curated way to introduce discerning travelers to the Sicily Beaugié knew and loved. “It was his idea, and then I joined,” she says. And The Thinking Traveller was born. From the outset, exclusivity was a founding principle. Every property in the portfolio is exclusively available through them.

 

“WE SAY WE TAKE ONLY PROPERTIES WITH SOUL . IT SOUNDS A BIT FLUFFY, BUT IT’S REAL.”

“It’s always been that way,” Beaugié says. “Exclusivity is the only way we can really invest in every single property. Not just in terms of marketing, but literally lending money to owners to build the pool, redo the bathrooms, and improve the space. We work in real partnership with the owners.” That model allows a level of control and care that’s rare in villa rental. “Because we manage all the bookings, we know every single client: who goes before, who goes after,” she explains. “We’re there holding hands with the owners, with the clients, and with the staff along the way.” One of The Thinking Traveller’s most remarkable achievements is its 40 percent repeat client rate, an impressive figure in a market saturated with choice. “Our portfolio is quite varied in size,” Rossella says. “We have everything from four- to fivebedroom villas – our core – up to amazing properties that work almost like private hotels, with 15 bedrooms and a resident chef.” That diversity reflects an equally varied client base. “We have a lot of multi-generational groups,” she explains. “Big families from the Middle East, for example. Privacy is paramount to them, and they love those large estates in Sicily and Puglia where they have total privacy. The properties are almost micro-destinations: tennis courts, spas, and huge grounds where you can jog inside your own estate.” There are also romantics: couples on honeymoons, or guests planning to propose in one of the smaller, more intimate villas.

 

“Our team and our owners love it when someone says, ‘I’m going to propose to my fiancée at this property,’” she says. “We organize the whole setting—it’s very special.” What unites these guests is not a demographic band, but a mindset. “People who come to us usually have tried other villa companies,” Beaugié notes. “But they say, ‘I haven’t had a better experience. I really feel much better being with you.’ That’s where the loyalty comes from. From trust.” For a company with such a strong reputation, The Thinking Traveller has expanded with remarkable restraint. In 25 years, they have moved slowly outward from Sicily, spreading intentionally across select parts of the Mediterranean rather than racing across the globe. Crucially, The Thinking Traveller never goes into a destination blind. “We explore; we see whether we can find the right small collection of villas to start with and the right people on the ground,” she says.

“For us, the team on the ground is essential. We’re entrusting them with our very special, very precious returning clients.” Every new region must meet a series of criteria: it must be the right destination within the Mediterranean; the initial collection must offer variety and value for money; the owners must be engaged, responsive, and aligned with The Thinking Traveller’s standards; and there must be a kind of indescribable ‘soul.’ “We say we take only properties with soul,” Beaugié explains. “It sounds a bit fluffy, but it’s real. Quality is the starting point, but there has to be something else. And if a property is amazing, yet I don’t get the right feeling with the owners, then it’s not going to work. We’re not developing hotels; we’re working in partnership with these owners.”

 

This year, The Thinking Traveller expands into Sardinia for the first time, something that’s been 15 years in the making. “There were incredible locations. But the mix of quality and amenities our clients expect just wasn’t there,” Beaugié reflects. “Many of the houses were used for the summer by politicians, by families from the Middle East or Russia. They’d send their staff ahead with their own curtains and their own things. That’s not what we do.” For guests, only a completely perfect property is good enough. So, only once they found Sardinian properties that could deliver that experience did they decide the time was right. “Now we’ve found villas that are absolutely perfect for what our clients need,” she says. “We feel very confident and excited.”

What makes The Thinking Traveller so different? Beaugié consistently returns to two things: deep, local knowledge and a commitment to tailored experiences. “Because our portfolio is small and exclusive, we can invest in our people,” she explains. “Our villa specialists—the team who talk to clients—go regularly to the destinations. They walk down the same streets, they stay in the villas, and they meet the owners.” There is a menu of tried-and-tested experiences: think wine tastings, in-villa cooking, and cultural tours. But the team is just as comfortable playing travel fairy godmother. “Sometimes people say, ‘We’re coming for my parents’ 50th wedding anniversary, and their dream is to have a soprano sing Vincenzo Bellini’s Norma by the piano in Catania,’” she says. “Then we go behind our core of experiences and build something completely bespoke.” For someone whose professional life revolves around other people’s holidays, Beaugié’s most treasured travel memories are strikingly simple. “For me, it’s really the quality time with our kids in a different setting,” she says. “We go to a new place, and we all appear in that new place at the same time.

We share experiences from a clean page.” Her three children are now grown—22, 20, and 18—and increasingly live their own lives. But travel, she says, has a way of drawing everyone back into the same orbit. “Last summer, we stayed in one of our Greek retreats,” she recalls. “Usually, they have their own agendas, but having breakfast together, knowing we had a chef coming in the morning, really set the tone for the day. We’d share that meal and then go on to share whatever the day brought. Experiencing things together, that’s very powerful.”

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Images: Instagram & Feature Image: Provided