The truth behind the Caribbean's A-list allure

They say diamonds are forever, but so is an Arne Hasselqvist-designed villa on Mustique – and frankly, we prefer the sparkle of the latter. The Caribbean has twinkled tantalisingly in the eyes of British travellers not merely for decades, but for centuries; Nevis’s Bath Hotel, built in 1778, attracted the naval commander Lord Nelson and the poet Samuel Taylor Coleridge to the hot springs. Even before the Second World War, the Caribbean was welcoming 100,000 tourists a year, but it was in the 1960s, when jets replaced steamships, that the region rapidly evolved into the glitzy, glamorous hedonistic idyll it is today.

“Why Mustique?” mused David Bowie in a 1992 interview with Architectural Digest. “Frankly, it was quite odd. I went down to spend a couple of days with Mick and Jerry in their house, and while waiting for the boat I came across this area of land attached to Arne Hasselqvist’s. And we talked about it, and I thought, ‘Why not?’”

Humans are divided into the haves and the have-nots… and the why-nots. The private island of Mustique, perhaps more than anywhere else in the Caribbean, is the adopted home of the why-nots. Mick Jagger, Bowie explains, came to Mustique via Princess Margaret. “Mick had been with that crowd for quite some time. He knew them all through the 1960s,” he said. “The Stones were of course the house band for all the coming-out parties in the 1960s. ‘Let’s get the Rolling Stones! Daddy, can we have the Rolling Stones?’”

It was in the Caribbean that rock ’n’ roll royalty and real royalty merged into the same flashy class of holidaymaker, lubricated by sun oil and martinis. Mustique was bought by the PR-savvy Lord Glenconner, Colin Tennant, for ￡45,000 in 1958, and by gifting his good friend Princess Margaret her own plot in 1960 he cemented the island’s reputation as a sun-kissed satellite of Swinging Sixties London and an abundant source of royal scandal and salacious rock ’n’ roll gossip. According to her friend the American vintner Tatiana Copeland, Margaret’s preferred whisky brand, the Famous Grouse, couldn’t be purchased on the island. “You had to make sure you had it when she came to your house,” Copeland said. “If you didn’t have her whisky then that was probably the last time she would go to you. If you couldn’t be bothered to know what she liked to drink, she probably wouldn’t be bothered to come back to you.”

With royals and rockers, and millionaires and models, the Caribbean already resembled a film set – and Caribbean scenery cropped up in all the most glamorous blockbuster movies of the 1960s, 1970s and 1980s. In Dr No, the 1962 Bond movie, Ursula Andress emerged from the Jamaican sea in a belted white bikini to meet Sean Connery… and that potent cocktail of sunshine, sand, sea and sex pushed Jamaica to the top of every jet-setter’s dream destination list.

Even in the notoriously iconoclastic 1990s and 2000s, no rocker or artist was immune to the charms of the Caribbean… Around 70 albums were recorded at George Martin’s Air on Montserrat, by legendary musicians including the Rolling Stones, Stevie Wonder, Michael Jackson, the Police, Sir Elton John, Lou Reed, Dire Straits and Duran Duran, who filmed the music video for their 1982 hit Rio on a yacht off the coast of Antigua. More recently, the Jamaican music studio-turned-resort Geejam played host to Amy Winehouse, Rihanna, Florence Welch, John Legend and Drake.

And while the jet set still jet into international airports and private runways, the Caribbean is perhaps best savoured by sea, with the classes embracing a slower, classier and more memorable way to enjoy multiple iconic holiday islands in one trip. In the latest Bond film, we find Daniel Craig in Jamaica, the island looking as louche, luxurious and lush as it did in Dr No. Decades on, the Caribbean still delivers decadent winter sun getaways to the rich, famous or fortunate… and tabloid pictures of the Rolling Stones.

Ernest Hemingway’s close relationship with the Caribbean is well-known; he wrote some of his bestselling novels at Finca Vigia, his large country house overlooking Havana, and entertained a starry stream of guests, including Gary Cooper and Ava Gardner. In the 1970s, his granddaughter, the model and actress Margaux Hemingway, continued his legacy of carousing in the streets of Havana. She is pictured here with her future husband, the French filmmaker
Bernard Faucher.

Princess Margaret was gifted her plot by her friend Lord Glenconner, Colin Tennant, who had purchased Mustique in 1958 for ￡45,000. In 1976, the News of the World published pictures of Princess Margaret and Roddy Llewellyn, with whom she had an eight-year affair while still married to the photographer Antony Armstrong-Jones. Llewellyn was a landscape gardener 17 years younger than the Princess, and the exposure of the affair led to her separation from Armstrong-Jones some two years later. Margaret and Llewellyn remained friends until her death in 2002 at the age of 71.

Despite leaving the island at 16 to pursue her music career, Barbados-born superstar Rihanna regularly returns for the annual Crop Over Festival in August, a traditional harvest celebration that was revamped into a national music and arts festival in 1974 by the tourist board and local businesspeople and musicians. She is also frequently spotted at high-end hangout The Sandy Lane Hotel, where she staged her 2012 interview with Oprah Winfrey, as well as Italian restaurant Daphne’s, and the local fast food roti chain Chefette.

The American photographer Slim Aarons captured a golden age of wealth, privilege, glamour and leisure, documenting the lives of authors, movie stars, business icons and high society. Many of his most enduring images were taken in Jamaica, snapping the stars hosted by the James Bond creator Ian Fleming, the writer and actor No?l Coward (whose naked pool parties were legendary) and the actor Errol Flynn. Katharine Hepburn, Alec Guinness, Laurence Olivier, Truman Capote, Clark Gable and Charlie Chaplin were among the Montego Bay set.

Long before it became a 21st-century model magnet, attracting the likes of Cara and Poppy Delevingne, Suki Waterhouse and Lily Donaldson, the private Caribbean island of Mustique provided the backdrop for a different era of rock star… and a different class of preposterously posey photograph. Throughout the 1980s and 1990s, David Bowie and Iman divided their time between his primary residence in Lausanne, Switzerland, and Mandalay…although they also kept a boat in the Mediterranean, and an apartment in Los Angeles. He described his Balinese-inspired home, Mandalay, as “a whim personified”.