When the plane comes into land in Montego Bay, the view isn’t quite the Caribbean I imagined during all those hours flying over the Atlantic. A line of mid-rise holiday resorts, uniform in their whiteness, bear down on the sea like a single gleaming fortress.

At the end of the runway at Sangster International Airport sits Sandals resort, where the staff wave and guests drink a toast as the deafening roar of yet another engine kicks up. The first all-inclusive resort on the island, it pioneered the democratisation of tourism in Jamaica, and many hotels like it followed with the dawn of cheap air travel.

This led to the expansion of Sangster airport in 2005, and it now handles around 3.7m passengers a year: Jamaica itself only has a population of 3m. At the weekends, the airport is so busy that harried visitors can pay an extra £20 to be escorted through security to Club Mobay, a VIP lounge that’s stocked with patties and Red Stripe.

Jamaica is the only island that’s surrounded by the Caribbean Sea. It has no Atlantic or Pacific coastline. So the winds are calm. It’s that calmness and security that nurtures and produces creatives. You see people all the time who come here and are totally changed by it

But there was a time when Jamaica was considered an exotic faraway playground for the super-rich. In the 1940s, as the HMT Empire Windrush was setting off to carry one of the first large groups of West Indian immigrants to Britain’s shores, some of our most illustrious figures were climbing aboard cruise ships to Jamaica looking for warmer climes and calming seas.

And they made just as indelible a mark on the island as the Windrush generation made on ours. Drive a little further from the coastline and the glamour is still there, gathered up inside some of the island’s most famous properties.

In fact, drive all the way up into the hills for 25 minutes and you’ll get to Round Hill, one of the oldest and most exclusive resorts in Jamaica. Luscious palms part to reveal pristine villas, most with wooden deckings, rocking chairs and private pools shielded from public gaze.

This 100-acre estate was once a sugarcane plantation that had profitable side hustles in pimento (allspice) and pineapples (an illustration of which adorns the resort’s logo to this day), overseen by Captain James Reid who owned 181 slaves at the time of his death, according to an inventory in the Jamaica Archives.

The private beach at Fleming villa

Round Hill is an unusual resort in that it’s actually a collection of private villas owned by the great and the good, with a modern spa, kids club and restaurant attached for convenience.

The man behind it all was John Pringle, a Jamaican-born socialite who bought 27 villas at Round Hill in 1952 and opened Pineapple House, which he turned into 36 guestrooms the next year. Today, those guestrooms are all designed by Ralph Lauren, who also owns two of the villas. He doesn’t rent them out, but the rest are let by their owners throughout the year.

The resort keeps the identity of the owners close to its chest, which is surprisingly easy to do, as they rarely come up for sale. Passed down through generations, there’s a five year waiting list with the average starting price of $3m.

The list of past owners include Viscount Rothermere (owner of the Daily Mail) who was the original owner of Villa 3; John F and Jackie Kennedy honeymooned in Villa 10; and legendary composer Oscar Hammerstein met Maria Von Trapp while owner of Villa 12, inspiring him to write The Sound of Music.

Winston Churchill painting at Jamaica Inn. The framed photo is still on display at the resort

Outside the villa marked Reid’s End, you’ll come to exactly that, the tombstone of the naval officer located among the immaculate foliage. This grisly memorial hasn’t stopped this four bedroom villa being the preferred retreat for Paul McCartney and his family when he comes to stay. A framed photo of Macca beaming among legions of staff sits on the kitchen countertops and it’s also a favourite spot with the younger members of the Royal Family.

With its quaint library, bamboo beds and colonial bar, Round Hill is like stepping back in time. There are no TVs in the white wooden-slatted villas, the pathways are lit by candelight after dark and afternoon tea is served promptly at 4pm.

Food for the restaurant is grown in an allotment on site, infusing the whole property with the smell of sandalwood, allspice and lemongrass. The latter is good for fever, I’m told by the groundskeeper. And don’t go near lizards, they’re bad luck, unless one of them jumps on you. That means you’re pregnant.

Perhaps because of the presence of so many former plantations and burial grounds, stories about ghosts, or “duppies” as they’re known locally, are everywhere. The most famous is also associated with the great house of another plantation.

A lagoon cottage at GoldenEye

A 40-minute drive over to the other side of the Bay will take you to Rose Hall, an imposing Georgian mansion that was once home to Annee Palmer, an English/Irish “white witch” who married John Palmer, the owner of the enormous plantation. Furnished with European antiques and chandeliers, its incongruency with the landscape only adds to a creeping sense of unease as you tour it. The story is a gruesome tale in which Palmer killed two of her husbands and numerous slaves before she was killed herself by a slave called Takoo.

Now owned by a former Miss World USA, the house was restored in the 1960s, but immortalised for all eternity in a Johnny Cash song. He penned “The Ballad of Annee Palmer” while living at a great house nearby called Cinnamon Hill, where he spent the latter days of his life with his wife June Carter. “At night I hear you riding/And I still hear your lover’s call/And I can still feel your presence/Around the great house at Rose Hall,” our guide sings next to Annee’s assumed tomb.

Legendary figures also loom large further along the coastline – 89km to be exact – at Jamaica Inn, a 50-room boutique hotel in the town of Ocho Rios. It was here, in 1936, that British parliamentarian and vice-chairman of the Conservative party Sir Harold Mitchell bought the great house at Prospect Plantation, introducing a diverse crowd to the delights of the island, not least Charlie Chaplin and Sir Winston Churchill.

Noel Coward's statue at Firefly

However, the bulldog himself chose to stay in Room 21 at nearby Jamaica Inn and, though he was only there for two weeks, the picture of him painting in the suite, wearing a hat and white mack despite the heat, has imprinted on the property itself. The original is framed in the bar, along with photos of the Kennedys and Marilyn Monroe, and the room itself goes by the moniker White Suite or the Churchill Suite.

Having driven an hour and a half to see it, however, I was told I couldn’t enter because American documentary maker Michael Moore was camped out in there and I wasn’t to disturb him. On the way out I ran into Peter Morrow, who with his brother is the third generation of his family to own and run Jamaica Inn. He was lounging on a wicker chair in the reception, greeting guests as they checked in.

At just under a two hour drive from either of Jamaica’s international airports, Jamaica Inn is a place you seek out rather than drop into. But Morrow has a compelling theory; so many people – from singers to authors to painters – make the effort because of its seclusion, which are integral to the creative process.

“Jamaica is the only island that’s surrounded by the Caribbean Sea. It has no Atlantic or Pacific coastline,” he says. “So the winds are calm. It’s that calmness and security that nurtures and produces creatives. You see people all the time who come here and are totally changed by it.”

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Two people who found exactly that are James Bond author Ian Fleming and all-round artistic party animal Noel Coward. Tales of Fleming’s dalliances in Jamaica follow you all over the island. He was supposedly a regular guest at Prospect Plantation and even came up with the “shaken not stirred” martini at the Jamaica Inn bar. But GoldenEye is where all these tales converge into an epicentre.

Fleming first laid eyes on Oracabessa Bay in 1942 as a naval commander when he was sent there on an investigation codenamed GoldenEye. Four years later, he saw 15 acres of this tropical overbrush is for sale and built his dream villa, naming it after the operation. His good friend Noel Coward came to visit and bought a beach villa, but found himself besieged by glamorous guests. So he built an escape from his beach retreat further up in the hills and called it Firefly.

Meanwhile, Fleming was bashing out 2,000 words a day and finished all 13 of his Bond novels in his sparse, bachelor villa, complete with private cove. Coward became known for his lavish cocktail parties and skinny dipping in the early hours, with the likes of Elizabeth Taylor and the Queen Mother in attendance, although the latter’s skinny dipping is unconfirmed.

Other public figures who visited Fleming included Prime Minister Anthony Eden, who keen watchers of Netflix series The Crown will know took three weeks sick leave from government to convalesce in Jamaica – at GoldenEye. On leaving, he planted a tree in the garden, starting a tradition that has survived to this day. A faded wooden notice at the foot of one marks Bill and Hillary Clinton’s stay there during his Presidency.

After Coward and Fleming’s death, the properties were bought by Chris Blackwell of Island Records, the label that brought reggae music to the wider world. Bob Marley was given the opportunity to buy Fleming’s villa, but found it “too quiet”.

When Sting stayed there, he wrote The Police’s biggest hit, “Every Breath You Take”, and the commemorative gold disc is mounted on a wall in the den. For regular punters wanting to bask in the creative calm of Fleming villa, the nightly rate starts at $5,000 and reaches $9,000 during high season.

Being a savvy businessman, Blackwell built an entire resort around the Fleming legend, with private properties leased out for 200 nights a year. Gather round the bar before dinner in high season, and it feels like being inducted into a tropical private members club; everyone is keenly interested in who you are and what you do.

Yet, there’s a great spirit of independence at GoldenEye. Kayaks and snorkels are strewn about the place for anyone to wander off with as they please and you swim to the spa across a glassy, turquoise lagoon. The Fleming villa isn’t even off limits, as long as it isn’t occupied and you’re accompanied by a member of staff.

As is the Jamaican way, truly special moments are to found on hilltops. Firefly is a humble abode, barely touched since Noel Coward passed away. The bed he died on remains, as does the sheet music at his piano and the books on his shelves.

Though it’s possible to rent it out as an event space and for weddings, it feels too personal, too full of memories for all that. His grave lies to the left of a statue of him looking out onto his favourite view. Coward came here, he said, to find “the valuable peace.” As the sun set on the vista, I could see why the great and good went so far and paid so much to find it.

The Private Travel Company (www.theprivatetravelcompany.co.uk; 0203 553 7543) offers a 5 night luxury Jamaica itinerary from £2,315 per person including 3 nights at Roundhill on a B&B basis, 2 nights at GoldenEye on a B&B basis, private transfers, return flights, private Yoga Session at Roundhill, zipline adventure and spa treatment at GoldenEye. For any additional activities please visit www.theprivatetravelcompany.co.uk

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