A gentle breeze wafts through swaying palm trees that dot the glistening ivory sand. In this secluded cove along a private beach in Jamaica’s Oracabessa Bay, the azure ocean is crystal clear. There’s nary 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, snapping me out of my Caribbean reverie.

The skinny-dipping commander the gentleman is referring to is Ian Fleming, creator of the world’s most famous fictional spy.

In 1943, at the height of the Second World War, Fleming, then a high-ranking officer in British naval intelligence, was sent to Jamaica on a mission to investigate German U-boat activity in the Caribbean. After only three days on the island, Fleming was smitten. He decided his future would behold another mission: to write, he said, “the spy story to end all spy stories” in Jamaica. He returned in 1946 and built a small villa on a secluded cliff overlooking a coral reef beside Oracabessa, a sleepy village on Jamaica’s north coast.

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 series of all time, starting with Casino Royale in 1953. For nearly 20 years, he spent his winters here, penning 14 James Bond books and indulging in a life as intriguing as his fictional hero. 

“The commander loved this spot. He loved the colours of nature, the peacefulness, especially in the evenings,” says the elderly gentleman who introduces himself as Ramsay Dacosta, Fleming’s long-time gardener who still works on the storied property.

Today, more than 50 years after the acclaimed author’s death, his home and legacy in Jamaica live on. His original villa is now part of GoldenEye Hotel & Resort, an upscale coastal retreat featuring a cluster of chic cottages and suites set amid a backdrop of tropical greenery.


Goldeneye Lagoon Cottage

Excited to embark on the guided, Fleming-focused tour offered by the resort, I enter the gates of GoldenEye and wander past towering pineapple trees and meticulously kept gardens to Fleming’s former abode, a U-shaped bungalow with glassless windows looking out across the Caribbean Sea. I’m told the villa is decidedly more luxe (in size and decor) than it was when Fleming lived there, and yet there are remnants of his presence—including his original writing desks, where he penned his novels. 

Dropping my bags next to one of these desks, I head back outside to the villa’s private sunken garden to indulge in Fleming’s usual evening fare: martinis (shaken, not stirred) and a delectable meal of some of his favourite island staples—grilled red snapper fish, rice and peas and callaloo. Sated and sleepy, I slither into my mosquito-net-draped, four-poster bed and drift off into a cricket-serenaded dreamland.

The next morning, I wake to the smell of traditional Jamaican breakie—ackee and saltfish, another Fleming favourite—and gobble up the morning fare (an acquired taste) before descending 32 steps to Fleming’s beloved private beach to snorkel the local reef, just as he did most mornings. The reef is a mere 20 yards from the shore.

In the recently published book Goldeneye Where Bond Was Born: Ian Fleming’s Jamaica, author Matthew Parker writes, “Fleming’s favourite thing of all … was the reef, where he would spend hours floating, observing or hunting.” 

I soon understand why. As I swim along the vibrant orange-and-yellow-hued coral, I spy sea turtles, schools of brilliant parrotfish, elegant spotted stingrays, large-eyed squirrelfish, blue tang and eagle rays. The underwater world is both meditative and exhilarating, and I linger there for two full hours, emerging only when my hunger gets the best of me.

Back at the villa, Dacosta joins me for lunch and, as we dine on roasted cho cho (a vegetable similar to squash) and fresh fish, he recounts tales of colonial Jamaica during Fleming’s years, a time when the island’s glitterati included the likes of Errol Flynn and playwright Noël Coward, Fleming’s closest confidant.

That evening, I head to Coward’s mountain-perched home, called Firefly. About a 15-minute drive from GoldenEye and open to the public, the humble, one-bedroom hideaway offers a breathtaking view of the island, while paintings, photographs and other artifacts inside the home reveal Coward’s celeb-laden life in Jamaica.

The next day, it’s all aboard a motorboat to view, from afar, a few classic Bond film locations. (So far, two Bond movies have been filmed in Jamaica, Live and Let Die and Dr. No.) The boat lingers longest by Laughing Waters, a beach west of Ocho Rios where cool river water cascades directly into the warm Caribbean Sea. It is here where bikini-clad Honeychile Ryder (played by Ursula Andress) rises from the ocean to meet James Bond—an iconic scene from Dr. No, the very first Bond film.

Following the boat ride, I decide to see more of Oracabessa’s surroundings—the ones that kept Fleming coming back year after year. My guide, Michael “Mikey” Sutherland, a soft-spoken Rastafarian with a penchant for playing Bob Marley classics, takes me to Fisherman Beach, where Fleming would often fish for his evening meal, and then on to Port Maria. While the 15-minute coastal drive is beautiful, it competes with the following day’s hour-and-a-half drive southeast to Port Antonio. Hemmed in by the Blue Mountains on one side and the Caribbean on the other, lush lands give way to Jamaica’s fertile agricultural plains along this route, and coconut, banana and pineapple trees line the highways into town.

A short drive further into the interior leads to the Rio Grande, where a boatman steers me on a bamboo raft along the emerald river as it winds through moss-covered stone arches and under bamboo trees. The blazing sun beats down on this tropical paradise as I lie back and gaze at snowy egret birds and blue herons that flutter above. It’s a serene experience that makes me feel like a starlet escaping the limelight. Much, perhaps, like Fleming himself, who grew to love rafting on the Rio Grande after attending some of Errol Flynn’s legendary rafting parties here.

My guide pulls up to Belinda’s, a makeshift restaurant along the river where I enjoy the best curry chicken I have ever tasted. While there, I meet a self-proclaimed die-hard Bond fan from Sweden who is treating herself to a 007-inspired trip for her 50th birthday.

“I’ve wanted to come for the past 30 years to stay at GoldenEye,” Elivera Wiegers tells me. “Coming here has surpassed my expectations.”

I know exactly what she means.

Getting There: WestJet flies to Montego Bay nine times a week from Toronto.