Jimmy Buffett’s Love Affair with the Caribbean

Jimmy Buffett was many things — singer, songwriter, entrepreneur (and ultimately billionaire), and leader and inspiration to a legion of devoted “Parrotheads” who took his music and concerts and adopted it as a lifestyle.

Perhaps less recognized is Buffett’s role as an unofficial ambassador for Caribbean travel, music, and at least some extent, culture. “He was and will forever be the best spokesperson for the Caribbean,” said Sharon Pomerantz Strelzer, a longtime public relations representative and travel advisor for Caribbean resorts and destinations.

Buffett, who died on Sept. 1 as a result of skin cancer, was so successful at building and branding his Margaritaville empire since opening his first restaurant in Key West in 1987 that it’s easy for a casual fan to forget that after spending a few years busking in Key West, Buffett was a Caribbean resident by 1978, moving to St. Barts shortly after sailing to the island for the first time.

Buffett’s association with Key West was lasting and undeniable, but even a cursory review of his massive catalog of songs reveals countless references to his experiences flying, sailing, and simply enjoying the Caribbean.

Some of it was just for fun — 1996’s “Jamaica Mistaica” relates the story of Buffett’s plane (piloted by the singer and carrying legendary music producer Chris Blackwell and U2 singer Bono and his family) being mistaken for a drug smuggler by Jamaican police and almost getting shot down; he famous “Cheeseburger in Paradise” conveys the simple pleasure of finding a good hot meal in Tortola after a long Caribbean sail.

As other observers have noted, however, there was often a degree of poignancy mixed into Buffett’s lighthearted lyrics: 1979’s “Volcano,” a staple at Buffett concerts for more than 40 years, was recorded at AIR Studios in Montserrat and refers to the island’s smoldering volcano, which erupted and devastated the island a few years later. The song anticipates the anxiety of being driven from a Caribbean home with a mix of humor (“Where I go I hope there’s rum, not to worry mon soon come”) and dread (“But I don’t want to land in New York City, don’t want to land in Mexico, no no no”).

After the disastrous Soufriere Hills eruption in 1995, Buffett played the song in a concert to benefit Montserrat relief efforts. Through his charitable foundation, Singing for Change — funded with $1 from every concert ticket he sold — Buffett donated millions to programs all over the world, but especially the Caribbean, giving to support Haitian earthquake recovery as well as music programs, rehousing Cat Key, Bahamas residents after 2019’s Hurricane Dorian, and backing sustainable farming in Jamaica and Dominica, among other efforts.

Buffett’s songs were informed by a lifetime of Caribbean travel and an understanding of the culture that went much deeper than drinking at one of his Margaritaville restaurants. St. Barth, Antigua, Haiti, St. Martin (“For five wild years in L’Orient, the party never stopped…”) Barbados (“Thought I might sail down to Bridgetown, spend some time in the Barbados sun”), and Martinique (“Well now, if I ever live to be an old man, I’m gonna sail down to Martinique, I’m gonna buy me a sweat-stained Bogart suit, and an African parakeet.”) are among the many Caribbean destinations name-dropped in Buffett’s lyrics.

“He was the patron saint of Caribbean good times,” said Chris Frantz, drummer for Talking Heads, an ardent sailor who, along with his wife and bandmate Tina Weymouth, has called the Bahamas a second home since the 1980s. “Wherever you went down there, Jimmy had been there before you and had probably written a song about it.”

He inspired millions to visit the Caribbean, and few island destinations would willingly part with the legions of Buffett-inspired travelers. As a travel writer who has visited dozens of destinations in the Caribbean as well as attending Buffett’s shows for more than 20 years, I still count having a cheeseburger at Le Select in St. Barts — another Buffett favorite — on my personal bucket list.

“Don’t try to describe the scenery if you’ve never seen it,” sings Buffett in “Mañana,” written about a visit to Cane Garden Bay and a more pointed tourism pitch than you’re likely to hear from any island’s public relations firm.

Buffett once described his music as “drunken Caribbean rock and roll,” but also could be serious about his affection for the islands.

“I love the Caribbean through a sort of a strange way,” he said. “My grandfather was a sailing ship captain and he sang the calypso songs. So all this sort of amalgamation of material came in and came back out, and I learned to be a performer and that gave me the vehicle to do it.”

And while you can almost hear the smile behind lyrics like “I’ve got a Caribbean soul I can barely control,” the near-universal respect voiced for Buffett after his untimely passing extended well into the Caribbean, too.

“He was a man from Mississippi who lived like he grew up in Montego Bay,” said Adam Stewart, executive chairman of Sandals Resorts International. “Jimmy Buffett inspired generations of fans to appreciate the moment: bright blue skies, calm seas, and boat days filled with family and friends. Like every Caribbean soul, he knew worries could always wait. Life is meant to be enjoyed.”

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