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What sailing owes Jimmy Buffett

2018 August 23

He tells us in one of his sailing ditties that he’s the son of a son of a sailor. But he’s more than that—he’s a sailor himself. His latest sailboat graced the cover of the July/August issue of SAILING in a photograph of a turquoise-hulled 50-footer named Drifter carving a frothy white wake through turquoise Caribbean water. Yes, Jimmy Buffett is one of us. 

It says something about the allure of sailing that he’s made time to pursue it while building a net worth of more than half a billion (according to Forbes) as a song writer, singer, Broadway play producer and performer, satellite radio entrepreneur, merchandiser, resort and restaurant chain owner, author and idol of a legion of fans who even at Baby Boomer age or older aren’t the least bit embarrassed to be called Parrotheads.


Still going strong in his 70s, Buffett has received ample rewards in his rise from Key West barroom guitar picker to CEO of an entertainment empire, but not enough credit for his contributions to sailing. I aim to right that wrong by declaring Jimmy Buffett one of the most influential sailors of his era, and I’m not joking.

Without Jimmy Buffett there would be fewer sailors, a diminished sailing economy and a little less romance in our sport. 

Here’s why: Buffett was a force that helped power the growth of the bareboat charter phenomenon that energizes a large share of the sailing business world, supports sailboat builders and equipment makers and creates new sailors. 

Buffett was the muse, the piper, who led sailors and wannabe sailors to the Caribbean to rent sailboats and live the dream. 

To be fair, I should also credit Mount Gay rum. If Buffett was the generator of Caribbean sailing fantasies, Mount Gay was the lubricant.

The life Jimmy Buffett sang about was an impossible dream for his most ardent fans. He could sing, “I just dream of the ocean—God, I wish I was sailing again” and “I think about the good times down in the Caribbean sunshine,” but his listeners had jobs, mortgages, kids, responsibilities that kept them anchored to orderly lives. Except: The sailing enthusiasts among them could escape to Buffett’s world for a week or two by chartering a sailboat in the Caribbean, and they went in droves.

Soon, Buffett songs were rising from charter sailboats into the tropical air over anchorages in the BVI and the Windward and Leeward Islands. Inhibitions swept away by smooth Barbados rum in the boat drinks Buffett celebrated in song, the charter sailors could sing along with a refrain from “Son of a Son of a Sailor” that seemed to describe their getaway—“I went to sea for adventure.”

On Montserrat in the Leeward Islands, in pre-volcano days, a time early in Buffett’s career, I found pirated (poor quality) copies of Jimmy Buffett CDs and bottles of (excellent quality) Mount Gay rum for sale in a dusty grocery store for exactly the same price—$2.

Buffett’s first sailboat was a Cheoy Lee 33 ketch he bought with the modest proceeds from the sales of some early recordings. A solidly built Luders design, the ketch, with its clipper bow and long bowsprit, looked as salty as a little pirate ship, which was no doubt part of its appeal to Buffett, who as a colorful denizen of the weed-and-rum-fueled Key West scene fancied himself a piratelike character. 

He might have been the grandson of a sea captain, but that didn’t mean he was an especially competent sailor. Ryan White, in his breezy biography Jimmy Buffett: A Good Life All the Way, tells of a cruise to the Bahamas in the ketch, named Euphoria after an Oregon tavern in which Buffett had performed to some acclaim. Buffett and his pals were hopelessly lost in the rough, foggy Gulfstream until their radio direction finder picked up an AM radio signal from Bimini. They homed in on the signal until they heard waves breaking. One of his mates rowed ashore to find someone who could pilot the ketch into a safe harbor on Bimini and roused a fellow named Boaty the Loadie to come aboard and manage a safe landing.

Buffett stayed with the salty look in his next boat, a Cheoy Lee 48, a handsome 31,000-pound clipper-bowed ketch with lavish accommodations that he was able to buy because, according to White, money from “Margaritaville,” his first hit record, was “piling up.”

Buffett must have learned a lot about sailing in the interim between the two boats. His first voyage on Euphoria II was a successful 800-mile passage from Florida to St. Martin on a typically gnarly Atlantic.

Years later, Buffett showed an appreciation of traditional sailing beauty when he bought an original 26-foot Alerion sloop designed by Nat Herreshoff, followed by a Tofinou 9.5, a modern daysailer with traditional lines inspired by boats like the Alerion.

There’s nothing traditional about Buffett’s current boat. Drifter is a Surfari 50 designed by Ted Fontaine that anyone can buy off the production line at Pacific Seacraft for about $2.8 million. It has the plumb bow and vertical transom typical of today’s racing boats and high-performance cruisers, along with a big rig spreading more than 1,300 square feet of working sail area and a sprit for gennakers and asymmetrical spinnakers. Cruising innovations include what Bob Perry in his SAILING design review called an “open-air saloon” in lieu of a conventional cockpit and, get this, twin 80-horsepower diesels.

Though Buffett is hugely successful in his eclectic business endeavors and today looks more like a retired Rotarian banker bound for the golf course than a pirate, his escapist appeal seems just as robust as it was decades ago when sailors discovered him. Not that everyone appreciates that, however, like the New York Times reviewer who panned Buffett’s Broadway musical, “Escape to Margaritaville,” last spring.

“If you’re not drunk or a Parrothead, as Mr. Buffett’s fans are called,” the reviewer wrote, “you’re in trouble. Mr. Buffett’s denatured country-calypso ditties and horndog smarm seem awfully lowbrow.”

Guess what, the musical was a smash hit. I’ll bet there were plenty of sailors among those Parrotheads and lowbrow drunks imagined by the reviewer who enjoyed the rollicking show.

It doesn’t matter that Buffett doesn’t  get his due from snooty New York theater reviewers, but his lack of recognition by the sailing world is a serious concern. 

And so I propose that a lifesize statue of Jimmy Buffett be erected in a suitable spot in Caribbean latitudes, perhaps on Tortola on the site of  The Moorings base where bareboat chartering was born. 

He will be looking seaward, with a guitar in one hand and a bottle of Mount Gay in the other.