Key West Back in the Day: ‘The Last Mango ‘cruise — what could possibly go wrong?

The Last Mango Cruise was created to promote the 1985 release of Jimmy Buffett’s ‘Last Mango in Paris’ album. Album cover photo by Louis Sahuc

Carl Hiaasen is best known as a superb satirical writer, but he also makes great paella. I discovered that in 1985 on Ballast Key, a private island owned by Key West’s beloved “gentleman developer” David Wolkowsky, during a Jimmy Buffett extravaganza called the Last Mango Cruise.  

The cruise concept was simple … theoretically. Conceived as a contest to promote the 1985 release of Jimmy’s “Last Mango in Paris” album, it promised a three-day vacation, sailing cruise and beach party with Jimmy for five lucky winners and their guests — in Key West, where his first Margaritaville Store had opened nearly 11 months earlier. 

At the time, I was part of the small initial Margaritaville crew assembled by Jimmy and his far-seeing business partner, Sunshine Smith. I oversaw the store’s fledgling mail-order department, wrote the “Coconut Telegraph” newsletter and helped coordinate fan relations. 

Nothing in my job description mentioned serving Hiaasen’s paella or hijacking a trolley. 

The contest was scheduled Oct. 25-27, coinciding with the highlight weekend of the island’s over-the-top Fantasy Fest costuming and masking celebration. Jimmy and his good friend, legendary bar owner Captain Tony Tarracino — subject of the brilliant “Last Mango” story-song — would be grand marshals of the festival’s lavish Saturday night parade down Duval Street, leading it on a custom-designed float with the contest winners. 

With plans like that, we thought, what could go wrong? 

Key West bar owner Capt. Tony Tarracino inspired Jimmy Buffett’s unforgettable, ‘Last
Mango’ story-song about an aging adventurer. CONTRIBUTED

Then, at the Margaritaville Store’s tiny office, we got a phone call saying the contest winners were missing in the Miami airport. 

Eventually they were located and made it to Key West. We took them to dinner at Louie’s Backyard, the gourmet oceanfront eatery that Jimmy loved.  

The next morning, the Margaritaville crew and I joined Jimmy and the winners aboard a gorgeous sailboat owned by Ted Irwin, founder of Irwin Yachts. With Ted and Jimmy telling stories, we cruised across clear blue-green water to Ballast Key — which, thanks to Jimmy’s friendship with David Wolkowsky, was the site of a private all-day party and Buffett concert.

Arriving at the remote island, whose major structure was Wolkowsky’s rustic beach house, we were met by Jimmy’s buddy, Hiaasen. That day Hiaasen wasn’t a leading Florida journalist/author; he was a chef engrossed in creating the perfect paella, simmering rice and seafood and spices in a circular pan more than five feet wide. 

The winners settled on comfortable lounge chairs in the shade. While we served them cocktails and paella, Jimmy smilingly played their requests and some new songs. It was sheer magic — hot sun and sand, the mingled scents of salt air and paella, waves lapping the shore and the strains of Jimmy’s guitar. 

Key West bar owner Capt. Tony Tarracino inspired Jimmy Buffett’s unforgettable, ‘Last
Mango’ story-song about an aging adventurer. CONTRIBUTED

After we sailed back to Key West, however, the magic evaporated and chaos took over. The boat returned late. The Fantasy Fest parade began before the winners could join Jimmy and Tony on the grand marshals’ float. Our Margaritaville team got them to Duval Street on foot, but the float was so far ahead that we couldn’t catch it. 

That’s when I hijacked the trolley. 

It wasn’t just any trolley. It was part of the parade — carrying Key West’s favorite traditional band, the Junkanoos — and band members graciously welcomed the contest winners as they clambered aboard. 

The Junkanoos serenaded them with Caribbean melodies throughout the parade route, saving the evening with the improvisational serendipity that still characterizes Key West. 

Both Jimmy and Captain Tony are gone now, but their memories remain … in oft-repeated Buffett lore, local tales and the minds of contest winners. They also remain in the lyrics of “Last Mango,” the song that forever connects the two old friends — where one unforgettable line states, “Our lives change like the weather, but a legend never dies.” 

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