Inspiration

These Vintage Photographs Show the Glitz of Caribbean Vacations

Casinos, yachts, sports cars, and nightclubs—it's all in there.

May 15, 2020

The Caribbean—it's been a perennial travel favorite for decades. Those gentle blue waters. The velvet-soft sand. The pervasive island vibes. Each country and island has its own draw, but there was a time from the 1950s through the 1970s when few other destinations could compete with this sunny getaway. Whether famous, elite, wealthy, or all-of-the-above, travelers moved in packs between Jamaica, Barbados, Haiti, Puerto Rico, Cuba, and The Bahamas, gambling, sailing, and merrymaking along the way. If it sounds glamorous, it was—no less than the great Slim Aarons was there to photograph much of it, and many of his images are included in this gallery. These photos show the Caribbean in all its vintage glory, and provides some excellent inspiration for now. How we wish we could be there.

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Havana, Cuba, 1950
Sailors gather outside a cafe in Old Havana.
Slim Aarons/Getty
Port-au-Prince, Haiti, 1975
Haiti was a wildly popular vacation spot in the '70s. Here, several holidaymakers board dinghies or hang out in huts on the beach while being photographed by the legendary Slim Aarons.

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Montego Bay, Jamaica, 1955
Crew with British West Indian Airways board a smaller Viking aircraft at the airport in Montego Bay. Today called the Sangster Airport, it's right next to the water and makes for a scenic takeoff or landing.
Slim Aarons/Getty
Out Islands, The Bahamas, 1964
Sailing in the Out Islands, which include all of The Bahamas save for New Providence Island, where Nassau is, and Grand Bahama Island, where Freeport is located.

Slim Aarons/Getty
Nassau, The Bahamas, 1963
Bahamas Speed Week, an annual motor racing convention that was held in Nassau between 1954 and 1966. Not only did it feature the major racers of the day (Carroll Shelby and Bruce McLaren), it also drew celebrities and socialites.
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Exuma, The Bahamas, 1967
Sunbathing on the Traveler II yacht in Exuma in the '60s. Slim Aarons climbed the ship's mast to get the shot.

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Savannah Beach, Barbados, 1950
Two friends hang out in a hut on Barbados's Savannah Beach, with the vacation crowds just beyond them.
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Paradise Island, The Bahamas, 1968
The Versailles Gardens overlooking the pool at the historic Ocean Club, now a Four Seasons Resort, on Paradise Island. The French Cloisters in the background overlook Nassau Bay; the quarter-mile stretch of gardens includes sculptures from the 18th and 19th centuries.

Slim Aarons/Getty
Port-au-Prince, Haiti, 1975
The Habitation LeClerc was a popular resort getaway for the wealthy in the '70s. Chef Jean-Claude Roy poses beside a sculpture of a swan, laden with food and drink, ready to serve its guests staying in the hotel's 35 villas.
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Havana, Cuba, 1978
Margaux Hemingway, a supermodel and Ernest Hemingway's daughter, visits the Tropicana Club with future husband Bernard Faucher.

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Havana, Cuba, 1957
Jimmy Durante, an American actor, performer, and comedian, on stage at Havana's legendary Hotel National de Cuba. Set in the middle of Havana's city center, it's drawn the likes of Frank Sinatra, Ava Gardner, and even Winston Churchill, since it opened in 1930.
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Havana, Cuba, 1955
Dancers at Club Tropicana, Cuba's legendary cabaret club set in a six-acre garden on the Villa Mina.

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Havana, Cuba, 1957
American vacationers play craps at the casino inside the Hotel Nacional. The hotel still operates today, but Fidel Castro closed the casino in 1960.
Slim Aarons/Getty
San Juan, Puerto Rico, 1956
Sunbathers at the pool at the historic Caribe Hilton, set on a 17-acre peninsula near Old San Juan.

Slim Aarons/Getty
New Providence Island, The Bahamas, 1974
Leonard Dalsemer, a paper company executive and philanthropist, with his family at their villa in Lyford Cay, on New Providence Island, also photographed by Aarons.