A Tour of Ian Fleming’s Jamaica

Ursula Andress and Sean Connery in Jamaica for 'Dr. No'.
Ursula Andress and Sean Connery in Jamaica for 'Dr. No'.Michael Ochs Archives / Getty Images

Along a private beach in Jamaica’s Oracabessa Bay, the ocean is nearly transparent. There’s not a soul for miles. It’s tranquil. Hypnotic. A quantum of solace. “This is where I would see the commander swimming naked most afternoons,” says an older gentleman. The skinny-dipping commander he’s referring to is Ian Fleming, creator of the world’s most famous spy.

In 1943, at the height of the Second World War, Fleming, then a high-ranking officer in British naval intelligence, went to Jamaica on a mission to investigate German U-boat activity in the Caribbean. He brought along his childhood friend Ivar Bryce, and together the two took the Silver Meteor from New York to Miami – the same journey later replicated by James Bond and Solitaire (posing as Mr. and Mrs. Bryce) in Fleming’s novel Live and Let Die.


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Fleming landed on the island and found it a beautiful, undeveloped place with enough intrigue, history, and potential for danger to conjure up a backdrop for post-war espionage adventures. “When we’ve won this blasted war, I’m going to live in Jamaica,” he told Bryce after three days. “Just live in Jamaica and lap it up, and swim in the sea and write books.” Fleming had decided, he said, to write “the spy story to end all spy stories.”

He returned in 1946 with Bryce, and after seeing a naked girl swimming in the bay while scouting the land, built a small villa on this secluded cliff overlooking a coral reef in Oracabessa, a sleepy village on Jamaica’s north coast. Its unfettered lands of rough grass, weeds and bush, blue ocean, and intense tropical heat offered mystery, sex appeal, and a desire to throw back a martini, if even just to cool off in the sweltering Caribbean humidity.

Fleming on his private beach in Oracabessa Bay. (Harry Benson / Getty Images)

The villa, which Fleming named GoldenEye after a wartime plan he was involved in, served as his refuge and inspiration for writing one of the top-selling book series of all time, starting with Casino Royale in 1953. For nearly 20 years, he spent his winters there, penning 14 James Bond novels and indulging in a life as intriguing as his fictional hero.

“The commander loved this spot,” says Ramsay Dacosta, Fleming’s long-time gardener who still works on the storied property. “He loved the colors of nature, the peacefulness, especially in the evenings when he would often entertain guests.”

Today, more than 50 years after Fleming’s death, his home and legacy in Jamaica live on. His once sparse original villa has been renovated and is now part of GoldenEye Hotel & Resort, an upscale coastal retreat featuring a cluster of chic cottages and suites set amid a backdrop of greenery spread across 52 acres, owned by Island Records founder Chris Blackwell.

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Fleming’s U-shaped bungalow, with glassless windows that look out across the Caribbean Sea, is upgraded (in size and decor) from when Fleming lived there, and yet there are remnants of his presence — including his original writing desk, where he penned his novels. A gazebo Fleming constructed, where he liked to take notes, is now a fine-dining restaurant, while a bridge connects the villa side to the cottages with salt and freshwater infinity pools.

Guests can indulge in the adventures the author and his alter-ego once enjoyed. Down 32 steps from the resort is Fleming’s beloved private beach, where Dacosta says Fleming would swim and snorkel for hours to spy on sea turtles, schools of parrotfish, spotted stingrays, large-eyed squirrelfish, blue tang, and eagle ray amid orange and yellow coral. Sometimes he’d stay until the late afternoon before he would need to prep for guests and garden parties.

“Fleming’s favorite thing of all was the reef, where he would spend hours floating, observing or hunting,” Matthew Parker writes in GoldenEye: Where Bond Was Born. As Parker explains, this reef fueled countless Bond scenes, from the dramatic underwater action of Thunderball to character descriptions in several other novels. In Casino Royale, Le Chiffre watches Bond during the pivotal card game, “like an octopus under a rock.”


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Guests of GoldenEye are also privy to explore the surroundings forever immortalized as classic Bond film locations in Live and Let Die, Dr. No, and The Man with the Golden Gun. A motorboat ride will take you to Laughing Waters, a beach west of Ocho Rios, where a bikini-clad Honey Ryder (played by Ursula Andress) rose from the ocean to meet Bond in an iconic scene from the spy’s first film. Nearby is Dunn’s River Falls, the place where Sean Connery and Andress took a dip in the waterfall.

A 15-minute drive will land you in Fisherman Beach, where Fleming would often catch his evening meal, and then on to Port Maria, where Fleming and his wife, Ann, were married in 1952. The picturesque Port Maria is also home to Cabarita Island, which inspired Surprise Island, the fictional hideout of villainous genius Mr. Big from Live and Let Die. And nearby is Falmouth Crocodile Farm, where Bond, played by Roger Moore in the film adaptation, ran across the backs of a line of lounging reptiles to reach safety.

The tranquility of the surroundings feels like escapism at its best, offering an even greater understanding of what drew Fleming to this oasis.

“Would the books have been born if I had not been living in the gorgeous vacuum of a Jamaican holiday?” Fleming wrote, “I doubt it.”

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