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From GoldenEye to Eden Rock: The most iconic hotels in the Caribbean

16 August 2021• Written by Sophia Wilson

With adventuring aviators as founders, royalty as repeat guests and settings blessed by the gods, the Caribbean’s most-loved hotels have many a tale to tell. Sophia Wilson steps ashore to discover the histories and personalities of these tropical institutions...

GoldenEye, Jamaica

A beach hut at GoldenEye
Courtesy of GoldenEye

We have Jamaica to thank for Britain’s best-loved secret service agent, James Bond. Author Ian Fleming first visited the country as part of a British Naval operation called Golden Eye in 1942 and went back four years later to purchase six hectares of a former donkey racetrack overlooking a small cove in Oracabessa.

After designing his dream villa, which he named GoldenEye, he returned every winter to write. He created 14 Bond novels from the desk in his bedroom where he kept the jalousies shut so that he would not be distracted by the flowers and birds outside. “Would these books have been born if I had not been living in the gorgeous vacuum of a Jamaican holiday? I doubt it,” Fleming admitted.

Ian Fleming at his desk as it is today
Photo by Harry Benson/Express via Getty Images

When not on the island, he rented the villa to Noël Coward for £50 a week, until the noted playwright opted to build his own Jamaican retreat a couple of kilometres down the coast. The characterful duo raised the profile of Jamaica, and British luminaries including Evelyn Waugh, Lucian Freud and prime minister Sir Anthony Eden were all later guests at GoldenEye.

In 1976 Chris Blackwell, the founder of Island Records who had acted as a location scout for Dr. No in 1961, purchased GoldenEye. Blackwell has gradually added 10 hectares in small parcels of land to the original estate and it’s now set up as a 21-hectare hideaway that is still adored by creatives, including Johnny Depp, Pierce Brosnan, Naomi Campbell and Kate Moss (all of whom have planted trees on the property). “GoldenEye is not a typical ‘resort’ with a concrete building on a beach, but rather a collection of villas, cottages and beach huts spread around tropical gardens, beaches and coves,” says Marika Kessler, co-CEO of hotel management company Island Outpost.

For true Bond aficionados, there is only one place to stay: the Fleming Villa. It is still home to the original desk and typewriter where 007 was created, but Fleming’s lair has been updated with some subtle modern touches, including a media room and bar in his former garage. With a private pool and direct beach access, it also comes with a personal butler and a bevy of staff, ready to prepare your Martini, shaken not stirred.

Curtain Bluff

The five-star sanctuary with 72 rooms and suites spread out along the surf beach and up the bluff.
Courtesy of Curtain Bluff

After the Second World War, Howard Hulford, an American former fighter pilot, turned his hand to flying wealthy businessmen around the world. And one such flight changed not only the course of his life but also tourism in Antigua. “He was flying Philip Reed, the chairman of General Electric, who had a holiday home in the private Mill Reef Club, when he saw this bluff, flanked with one calm bay and another surf bay,” explains managing director Robert Sherman, who has worked at the hotel since 1978. “He immediately fell in love with the site and decided right at that moment that he was going to build his dream home on this location.”

All the suites have impressive beachfront views
Courtesy of Curtain Bluff

Unfortunately, it wasn’t quite that straightforward – Vere Bird, then-premier of Antigua and Barbuda, told the pilot that he could only have a private residence if he also built a hotel to bring tourists to the island. Undeterred, Hulford set about finding the necessary investment, and the hotel opened with  22 rooms in February 1962.

Hulford’s mantra was simple: “Take care of guests as if they are family” – and nearly 60 years later the hotel runs under the same ethos. A weekly cocktail party is still hosted at Lady Hulford’s house (Howard Hulford was knighted in 2008), afternoon tea is served daily on the Sugar Mill terrace and children are kept entertained by a band of watersports instructors and tennis pro Nigel. The result is a fiercely loyal clientele; some guests have been returning for 50 years, and staff are very much part of the family (among the 215 employees, the average length of service is 30 years). With a bright Caribbean aesthetic throughout (think patterned tiles and splashes of bright blues and greens) the hotel is welcoming rather than flashy but it does attract a sprinkling of celebs who come to shun the limelight – Paul McCartney spent time indulging his passion for painting at the hotel in the 1970s.

“Take care of guests as if they are family”
Courtesy of Curtain Bluff

The Hulfords’ impact on Antigua extends far beyond the scenic peninsula where the Caribbean Sea and the Atlantic Ocean collide. In 1967 Hulford worked with Desmond Nicholson to create Antigua Race Week, now a staple of the yachting circuit, and in 1974 the couple created The Old Road Fund. Guests of the hotel are encouraged to donate to the charitable foundation rather than leave tips, and the fund has so far invested more than $3 million (£2.3m) in the local community.

Eden Rock

Located on a rocky promontory surrounded by white-sand beaches and gin-clear water.
Courtesy of Eden Rock

Aviator and adventurer Rémy de Haenen proved his daredevil credentials when he landed the first plane on St Barths (touching down on the short runway still sends shivers down the spines of the most frequent of flyers). The former French merchant marine set up a local shipyard and an airline company and became the first mayor of St Barths. He also decided to buy a rocky crop of land in St Jean Bay. “The locals thought he was crazy to buy this rocky promontory, but he knew that this location was unique and was sure that hotels and tourism could develop on the island,” says general manager Fabrice Moizan.

With the help of a few locals, Haenen built himself a house on top of the rock from the blue stone found on the island. He and his wife Gisèle opened the home and surrounding cottages as a guest house in the 1950s and invited their illustrious friendship group. With the guestbook soon featuring David Rockefeller, the Aga Khan, Prince Rainier of Monaco, Greta Garbo and Jacques-Yves Cousteau, the property set St Barths as a whole on a path to becoming a playground for the rich and famous.

Prince Rainier III of Monaco was a guest at the hotel
Courtesy of Eden Rock

In 1995 Haenen sold Eden Rock to the British Matthews family, who set about restructuring it as a hotel without losing its eccentric homely feel (Eden Rock has never had a formal reception area, for example). Now part of the Oetker Collection, it reopened in 2019 after suffering extensive damage during the 2017 hurricane season. “We rebuilt the place keeping in mind its heritage, which has always meant the world to us,” says Moizan.

The island’s flagship hotel still features its signature bright-red colour palette and its 37 suites and villas are packed with quirky touches, including red rubber ducks and in-room cocktail kits. Part of the post-hurricane rebuild also includes the new beachside Rémy Bar, to honour the hotel’s founder. Designed to evoke his original home, the laid-back beach style encapsulates “the generous spirit he deployed when welcoming his friends to his home in the old days,” according to Moizan.

Sugar Beach

Located on the site of an 18th-century sugar plantation and its rooms are designed in a plantation style
Courtesy of Sugar Beach

As it sits directly between St Lucia’s majestic Piton mountains, it’s not surprising that this patch of land has been considered sacred for nearly 2,000 years, including by the island’s earliest inhabitants, the Arawak Amerindians. “Mountains were important in the Amerindian culture, as they saw them as the embodiment of gods,” says Sugar Beach’s associate director of PR, sales and marketing, Ruth Chaves. “The Arawaks chose the Petit Piton and Gros Piton to personify their deities.”

Despite its spiritual significance, it was British eccentric Lord Glenconner that introduced this area to an international audience. His son Henry came across the site, then owned by the Jalousie Estate, in 1979 while out walking, and Lord Glenconner decided to buy the plot. When he was later exiled from Mustique he moved lock, stock and elephant (he owned one, Bupa, as a pet) to the site. He went on to set up the Bang Between the Pitons restaurant and the foundations of the resort that exists today.

Matt Damon rented out the whole property to renew his wedding vows
Courtesy of Sugar Beach

Princess Margaret was a close friend of Lord Glenconner’s (his wedding gift of a plot of land on Mustique is what kick-started that island’s development) and she visited the Jalousie Resort (it’s now a Viceroy resort) many times in the 1970s and latterly in the 1990s. Prior to her visits she often sent a full wardrobe of clothes in advance. “Her fur-lined mackintosh was talked about a lot on the island, to the point that locals still chat about it,” says Chaves.

Nowadays you are unlikely to find any fur-clad royalty hanging out by Sugar Beach’s private plunge pools, but its enviable location still holds celebrity allure. Matt Damon rented out the whole property to renew his wedding vows and Gwyneth Paltrow is also a fan of its relaxing powers. Colourful tuk-tuks run guests from the palm-lined beach back to their brilliant white suites, where a private butler is never more than a call away. One imagines Lord Glenconner and Princess Margaret would have approved.

Rosewood Little Dix Bay

The hotel lies on Virgin Gorda’s west coast
Courtesy of Rosewood Little Dix Bay

Sustainable luxury may be commonplace these days, but when businessman and conservationist Laurance S Rockefeller came across this 800-metre stretch of white sand beach in 1958, his vision for an eco-friendly hotel was revolutionary. “Planning for the original property included experiments in harnessing natural sources of energy to supply power and water, as well as thoughtful design to minimise interruption to the island,” says Andreas Pade, managing director of Rosewood Little Dix Bay, which lies on Virgin Gorda’s west coast.

The Queen and the Duke of Edinburgh visited the hotel during their Caribbean tour of 1966
Courtesy of Rosewood Little Dix Bay

When the property opened in 1964 its barefoot vibe (which included no air conditioning and a ban on in-room televisions and telephones) proved to be an instant hit with the New York set, who knocked back Pelican Smashes (a potent mix of rum, whisky, bourbon, pineapple, orange and guavaberry) while taking in the pristine environment. Two years after it opened, the Queen and the Duke of Edinburgh gave it the royal seal of approval, putting not only the resort but also the BVIs on the map. “Little Dix Bay provided local employment and economic development to the destination, bringing some of the coveted Caribbean tourism trade to the small but picturesque island,” adds Pade.

Its "barefoot vibe" was a hit with guests
Courtesy of Rosewood Little Dix Bay

The Rockefellers sold the hotel to Rosewood Hotels and Resorts in 1993. Following its golden anniversary the property closed for renovation – and just months before it was set for a grand reopening Hurricane Irma pounded the property. Undeterred, Rosewood brought in New York-based design studio Meyer Davis to reimagine the property, while staying true to Rockefeller’s original vision.

“The resort celebrates the energy of the 1960s in a contemporary, eco-friendly manner, with the footprint and structures of the property remaining the same,” says Pade. One such structure is the four-corner, vaulted ceilings of the resort’s Pavilion restaurant, which somehow survived the wrath of Irma. The eatery now serves up fresh produce from the resort’s on-site farm, a new addition as part of the redesign, but a Pelican Smash is still the house speciality in the adjoining Rum Room.

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