The Thinking Traveller

Building a travel brand legend, specialising in high-end exclusive villas and experiences.

Invested £7M in 2020

Rossella and Huw founded The Thinking Traveller in Sicily in 2002, embarking on a voyage around the Mediterranean that continues to inspire them. From 220 in 2020, today it has 325 highly curated properties priced at £3-£80k per week, all 100% exclusively available to rent through The Thinking Traveller. This includes some of the most sought-after villas in the Mediterranean, such as the 16th Century former fortress Forte San Giorgio on the island of Capraia and the aristocratic hilltop Rocca delle Tre Contrade in Eastern Sicily. Sales grew to £20m in 2019 with more than half of clients from outside the UK and especially popular with US travellers. 

In 2020, we partnered with the founders and joint-CEOs Huw and Rossella Beaugié and their team in the next stage of growth. They were joined by Ian Simkins as Executive Chairman, former CEO of Audley Travel, who helped to grow it into a £250m global business.

In Athens in 2008, they met Dimitris and Anna, who had started White Key, a business with similar values . In 2021, the two companies joined forces and 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.

Their passion for the destinations – southern Italy, Greece and Corsica – and their deeply held values are encapsulated in their mission: to be the most desirable, respected and thoughtful villa rental company in the world.

Popular with multi-generational families, couples and groups of friends, the brand is renowned for its award-winning personal service and the expertise of its in-destination local managers. They provide clients with a 24-hour concierge service and a range of curated experiences to help make their holidays truly memorable, booking guided cultural tours and excursions, in-villa culinary experiences and chefs, yacht charters and yoga teachers. Their obsession of seeing everything through the lens of their clients and villa owners is echoed in their impressive company’s customer satisfaction NPS of 87 and the business being voted Condé Nast Traveller readers’ Best Villa Rental Company every year since 2016.

The business also impressed us with their understanding of the needs of their villa owners, many of whom had been with them exclusively for over ten years and half of whom had never rented out their villa with anyone else. Above all else, owners chose to partner with The Thinking Traveller because they were proud to be associated with a brand that attracts the highest calibre of clients.

Our investment helps the business curate a broader selection of exclusive villas in new destinations around the Mediterranean through strategic acquisitions and partnerships as well as marketing the brand further in its core markets including the UK, Europe the US and Australia, and scale the team to ensure clients and owners continue to experience excellent service and support.

Piper was our first choice when looking for an investment to drive our brand to the next level, and we are delighted to be working with their team. It’s a difficult time for the travel sector, but thanks to Piper’s expertise, patience and always thoughtful approach The Thinking Traveller has a very bright future indeed.

Huw Beaugie, co-founder of The Thinking Traveller

Current investments