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How Stella Got Her Groove Back, 1988
Kevin Rodney Sullivan
Work-obsessed banker Stella (Angela Bassett) jets to Montego Bay, Jamaica, for a holiday with her wise-cracking friend (played by Whoopi Goldberg). Between dips in the pool and beach-side cocktails, Stella finds her groove in the arms of a much younger Taye Diggs in this May-September island romance.
Siméon, 1992
Euzhan Palcy
In this colorful, fantastical, music-filled film, the director returned to her native Martinique to tell the story of Siméon, a music teacher helping to realize the potential of his pupil, Isidore. The two have a dream to share their island s rhythmic musical sound, Zouk, with the world, and do so with the help of Isidore s adorable 10-year-old daughter. The delightful film flip flops in and out of reality (Siméon is at one point a ghost) and the overall effect is one of a Caribbean candyland.
Island in the Sun, 1957
Robert Rossen
One of the first movies filmed on the islands of Barbados and Grenada, Island in the Sun is the film adaption of Alec Waugh’s novel of the same name. The film reveals the obvious class divide and deep rooted racism experienced by the island’s native people and their British colonizers. The story unfolds with the forbidden love between David Boyeur (Harry Belafonte) and Mavis Norman (Joan Fontaine) and a political race between Boyeur (an island native seen as the underdog) and Maxwell Fleury (a white plantation owner’s son) played by James Mason. Controversial at the time (1957) for its representation of romance between its black and white characters, the film represents something of a milestone in Hollywood.
Guava Island, 2019
Hiro Murai
Cast with Afro-Cuban locals, Donald Glover a.k.a Childish Gambino’s musical short film, just under an hour long, tells the story of the fictitious Guava Island. It’s a breezy Caribbean island (shot on location in Cuba) controlled by a harsh paramilitary group called Red Cargo. A musician named Deni Maroon (Glover) lives there with his girlfriend Kofi Novia (Rihanna) and together, they decide to put on a music festival. The film expanded on Glover’s “This is America” music video and suggests that despite the setting, Guava Island is far from a paradise.
Our Man in Havana, 1959
Carol Reed
Hoping to make an extra buck to pay for his spoiled daughter s country club membership, vacuum salesman Alec Guinness agrees to become a British spy in Havana. As you can imagine, things go awry when he falls in love with fellow spy Maureen O’Hara and becomes a target himself. Watch for city scenes of 1950s Havana in black and white.
Dr. No., 1962
Terence Young
The original film that launched the ongoing cinematic saga of James Bond starred Sean Connery as Agent 007. Set in Jamaica, where Ian Fleming wrote the majority of the Bond series from his estate at GoldenEye, the film cast Ursula Andress as shell diver Honey Rider, who emerges from the crystal blue waters in St. Ann’s Bay, in the now iconic white bikini clad with a tool belt.
The Tamarind Seed, 1974
Blake Edwards
In what sounds like a James Bond plot, an English civil servant (Julie Andrews) falls in love with a Russian agent (Omar Sharif) on holiday in the Barbados. Between all the twists and turns, there are lovely scenes of Andrews walking the beach at dusk.
7 Days in Havana, 2012
Gaspar Noé, Elia Suleiman, Juan Carlos Tabío, Laurent Cantet, Pablo Trapero, Benicio del Toro, Julio Medem
Watching this film transports viewers directly to Havana. As its title suggests, the story unfolds over seven days spent in the Cuban capital, with each day’s lensed by a different director. Characters weave in and out of the week-long plot, lives intersect, and Havana is seen and experienced by many different eyes.
Cocktail, 1988
Roger Donaldson
In this ’80s classic, Tom Cruise plays a charming New York City bartender by night to pay for his business degree by day, but his unexpected success takes him to stint at a Jamaican resort and eventually leads to him opening his own bar.
Cool Runnings, 1993
Jon Turteltaub
Loosely based on the true story of the Jamaica national bobsledding team at the 1988 Winter Olympics, Cool Runnings begins in sunny Jamaica (filmed in Discovery Bay and Kingston). Two runners fail to qualify for the Olympics are sprinters and are encouraged to form a bobsled team to represent their country at the Olympics. The hilarious film then follows the group of four Jamaicans to frigid Calgary. There’s nothing not to like about this movie.
Thomas Crown Affair, 1999
John McTiernan
An art theft investigator (Rene Russo) falls for the prime suspect in her latest case (Pierce Brosnan), unable to deny his suave charm. Unlike the original 1968 film starring Steve McQueen, in which he whisks his love interest off to a New England beach, the remake has the romance unfold at Mr. Crown s own villa in Martinique—a little slice of paradise.
Die Another Day, 2002
Lee Tamahori
The image of Halle Berry emerging from the Cuban Caribbean water in a diving bathing suit reminiscent of Ursula Andress in the original Bond film, Dr. No, would keep us alive another day too.
Pirates of the Caribbean, 2003
Gore Verbinski, Joachim Rønning, Espen Sandberg, Rob Marshall
A total of five films (with a sixth on the way) following the misadventures of the swashbuckling pirate played by Johnny Depp were filmed throughout the Caribbean—from Dominica to the Bahamas to Saint Vincent and the Grenadines to Saint Lucia. Each of the locations are as epic as the tale of Captain Jack Sparrow.
Dirty Dancing: Havana Nights, 2004
Guy Ferland
A remake of the 1987 original, set in Havana, Cuba (although filmed in Old San Juan, Puerto Rico), during the Cuban revolution. American girl Katey (Romola Garai) meets local boy Javier (Diego Luna) and the two enter a salsa dance competition (and a sensual romance).
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