When Jimmy Buffett and Captain Tony Led Fantasy Fest

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Jimmy Buffett, right, and Captain Tony Tarracino serve as co-grand marshals of the 1985 Fantasy Fest Parade in Key West. PHOTO: Gary Bergmoser

The Last Mango Parade: When Jimmy Buffett and Captain Tony Led Fantasy Fest

In October 1985, Jimmy Buffett and Captain Tony Tarracino climbed aboard a custom-designed float and led the infamous Fantasy Fest Parade down Duval Street.

Their appearance as co-grand marshals came at a remarkable moment in their long friendship. Buffett had just released Last Mango in Paris, turning Tony’s adventures into the title song of his new album, while Tony was campaigning to become mayor of Key West with Buffett serving as his honorary campaign manager.

But another story was unfolding behind the parade. A national contest had brought five Buffett fans and their guests to Key West for a weekend that promised sailing, a private island performance and a place alongside Buffett in Fantasy Fest.

What happened next brought together music, friendship and some of Key West’s most memorable characters—and produced one of those stories that could only happen here.

The official poster for the 1985 Fantasy Fest, held October 23–27 under the theme “Broadway Fantasies.” IMAGE COURTESY OF DORIAN PATTON

A Party Created for Key West

Fantasy Fest itself was still relatively young.

The celebration was born in 1979 after a disastrous summer tourism season marked by gasoline shortages, water rationing and hurricane threats. Key West business owners Joe Liszka, Tony Falcone, Bill Conkle and Frank Romano envisioned a Mardi Gras-style festival that could bring visitors to the island during one of its slowest times of year.

The first Fantasy Fest lasted three days and included costume balls, calypso music and a Saturday night parade featuring 26 floats. About 7,000 spectators lined Duval Street. That first year, a free-spirited Old Town character and local thrift store owner who went by “Sister” famously painted her entire naked body in silver and gold, climbed on top of a convertible and rode down Duval Street as part of the inaugural parade. This instantly set the tone for the event, solidifying the decadent, uninhibited spirit for which Fantasy Fest became known worldwide.

Fantasy Fest is run by the nonprofit Tourism Development Association, or TDA (not to be confused with the Tourist Development Council, or TDC, which collects local bed taxes to fund Key West advertising). For decades, the festival operated under the direction of The Market Share Company, owned by Linda O’Brian and Ann Dickinson.

By 1985, Fantasy Fest had grown into a five-day celebration. Held October 23–27, that year’s official theme was “Broadway Fantasies.” The timing presented an irresistible promotional opportunity. Buffett’s management was building a national campaign around Last Mango in Paris, the new Margaritaville Store and a contest that would bring fans to Key West during Fantasy Fest. Pairing Buffett with Captain Tony—the real-life inspiration behind the album’s title song—gave the promotion its natural Key West centerpiece while bringing national attention to the festival.

Under O’Brian’s direction, the TDA named Buffett and Captain Tony co-grand marshals of the Saturday night parade. It was perfect casting for “Broadway Fantasies”: two larger-than-life Key West characters leading the island’s biggest show down Duval Street.

Jimmy Buffett performs at Captain Tony’s Saloon in 1979, years after beginning his Key West career in the island’s bars. Captain Tony and his stories would later inspire the title song of Buffett’s 1985 album, “Last Mango in Paris.”

PHOTO: Keith Terracina

The Character Behind “Last Mango”

Long before he became the central character in a Jimmy Buffett song, Captain Tony had already lived enough lives for several men.

The fisherman, gambler, bar owner, reputed gunrunner and master storyteller had arrived in Key West in 1948. He eventually took over the Greene Street bar that became Captain Tony’s Saloon, where generations of locals, sailors, writers, musicians and visiting characters gathered beneath a ceiling covered with business cards, bras and pieces of Key West history, including a massive ficus “Hanging Tree” used for public executions that predated the dive bar by more than a century.

Jimmy Buffett became part of that world after arriving on the island in the early 1970s. He played at Captain Tony’s during his early Key West years and, according to the saloon’s history, was sometimes paid in tequila and baloney sandwiches. Over time, their friendship came to resemble that of a father and son—which says something, considering Tony had 13 children. He later joked that feeding Buffett had been the best investment he ever made.

Tony was more than the guy who gave Buffett a place to play. He was the kind of character Buffett found throughout old Key West: weathered, independent, enormously entertaining and never inclined to let absolute accuracy interfere with a good story.

Buffett turned many of the people he met in Key West into songs. In early 1985, Captain Tony’s stories would become the basis for one of his most memorable.

The song began taking shape that February, when Coral Reefer Band keyboardist Mike Utley visited Buffett in Key West. Utley came up with the title “Last Mango in Paris,” a play on the scandalous 1972 Marlon Brando film Last Tango in Paris. The phrase stuck, and on his flight home to Los Angeles, Utley began working out the melody, chord progression and framework for the chorus on a legal pad.

A few months later, he brought those beginnings to a Nashville writing session with Buffett, Will Jennings and Marshall Chapman. Together, they shaped the song around Captain Tony’s colorful life. Set inside Tony’s Key West saloon, it unfolds as a conversation with an aging adventurer sharing tales of distant places, narrow escapes and a life lived without much regard for convention.

The song was less a literal biography than the distilled essence of Tony - a man looking back on a life fully lived while reminding a younger friend that there was still much left to do. The chorus was drawn from a line Tony had grumbled to Buffett years earlier at the bar: “Jimmy, there’s still so much to be done.”

Released in 1985, Last Mango in Paris transformed Tony from a legendary Key West personality into part of the wider Buffett mythology. It also captured something real about their friendship. Buffett understood the value of Tony’s stories, while Tony had watched Buffett grow from a young musician playing island bars into one of the country’s most recognizable touring artists.

The bar became an immediate goldmine. Fans packed the historic building - which had served as a 19th-century icehouse and morgue - to sit under the hanging tree, drink beneath the rafters lined with signed dollar bills and catch a glimpse of the real deal Captain Tony.

Jimmy Buffett and legendary treasure hunter Mel Fisher capture a monumental moment in Key West history July 20, 1985, the exact weekend the Nuestra Señora de Atocha mother lode was finally discovered. PHOTO: Don Kincaid

Music, Treasure and a Run for Mayor

Many of the stories converging in Key West in 1985 had roots in the Chart Room.

Key West developer David Wolkowsky built the Pier House in the late 1960s and created the Chart Room inside it. The unpretentious bar became a gathering place for the island’s musicians, writers, treasure hunters and assorted characters—and one of Buffett’s first haunts after he arrived in Key West with Jerry Jeff Walker in 1971.

Wolkowsky is widely credited with giving Buffett one of his earliest Key West jobs. He soon became more than an employer, helping introduce the young musician to a literary circle that included Truman Capote, poet John Malcolm Brinnin and writer Dotson Rader.

The Chart Room brought Buffett into an even broader cast of Key West characters. Bartender, photographer and writer Tom Corcoran became one of his closest friends. Another Chart Room bartender (and Carol Shaughnessy amore), Phillip “Phil” Clark, regaled Buffett with stories of Caribbean adventures, treasure hunting and smuggling that helped inspire “A Pirate Looks at Forty.” Mel Fisher and members of his crew used the bar as an unofficial headquarters, and Buffett also crossed paths there with musicians, writers and adventurers including Jim Croce, Hunter S. Thompson and his future brother-in-law, writer Thomas McGuane.

In 1974, Wolkowsky purchased undeveloped Ballast Key and transformed it into a private island retreat about nine miles from Key West. He regularly welcomed friends there, including Buffett, along with writers, musicians and other unconventional figures from the world he had cultivated around the Pier House. That longstanding friendship would later make the island the setting for the Last Mango Cruise.

By 1985, the young musician Wolkowsky had once paid in drinks was a successful recording artist and major touring draw. That year helped mark Buffett’s transition from popular singer-songwriter to the center of a growing cultural phenomenon. Last Mango in Paris reached the Top 10 on Billboard’s country albums chart, while his first greatest-hits collection, Songs You Know by Heart, arrived that October and eventually became the best-selling album of his career.

Buffett and business partner Sunshine Smith had also opened the first Margaritaville Store at Land’s End Village earlier that year. Long before Margaritaville became an empire, it was a scrappy Key West shop where a handful of employees sold merchandise, filled mail orders and did whatever else needed doing.

That summer, another member of the Chart Room circle made history.

On July 20, 1985, after more than 16 years of searching, Mel Fisher’s crew discovered the main treasure pile of the Spanish galleon Nuestra Señora de Atocha off the Lower Keys. The recovery of gold, silver and emeralds worth hundreds of millions of dollars electrified Key West and finally fulfilled Fisher’s longtime morning declaration: “Today’s the day.”

The following day, Buffett joined Fisher and the Golden Crew aboard the salvage boat J.B. Magruder to celebrate. With recovered silver bars stacked on deck, Buffett brought out his guitar as the crew savored the discovery that had finally ended their long search.

VOTE TONY: Campaign manager Jimmy Buffett joins candidate Captain Tony Tarracino inside Captain Tony’s Saloon during the 1989 Key West mayoral race. Tarracino won the tight election by just 32 votes, unseating incumbent Tom Sawyer on an anti-overdevelopment platform. PHOTO: SALVATORE “SAL” TERRACINA

Meanwhile, Captain Tony was making his third run for mayor

Campaigning under the slogan “Save, don’t pave, our shoreline,” Tony opposed overdevelopment and promised to preserve the eccentric, independent character of Key West. Buffett joined the effort as his honorary campaign manager.

Buffett often retold the story of the night Tony decided to run in 1985. A group of corporate developers had unveiled plans for a massive condominium complex that would block the historic island waterfront. According to Buffett’s recollection, Tony slammed his fist onto a bar table and declared, “Goddammit. I’ll fight these condo bastards if no one else will. I’m gonna run for mayor.”

The December 1985 runoff, which was delayed by a couple of weeks after Hurricane Kate brushed the island, ended with bank vice president Tom Sawyer defeating Captain Tony by exactly 52 votes.

Four years later, Tony made his fourth run and finally became mayor, beating the incumbent by just 32 votes out of more than 6,000 cast. His famously unvarnished campaign slogan was: “All you need in this life is a tremendous sex drive and a great ego. Brains don’t mean $hit.”

Tony served a colorful two-year term focused on limiting growth, protecting the island’s eccentrics and preserving Key West’s daily sunset celebration. Buffett proudly told reporters that Key West had chosen a “fictional character” over a standard bureaucrat to protect the soul of the island.

And character he was.

An original promotion from MCA Records and Frontline Management advertises five grand-prize trips to Key West for the “Jimmy Buffett Last Mango in Paris Cruise,” including airfare, a sailing excursion with Buffett and a private beach party and performance. The trip was scheduled for October 25–27, 1985, during Fantasy Fest weekend. IMAGE COURTESY OF CAROL SHAUGHNESSY

The Last Mango Cruise

Back in October 1985, before the votes had been counted, several pieces of Buffett’s expanding Key West world were coming together. His first Margaritaville Store had opened earlier that year, Last Mango in Paris had introduced Captain Tony’s stories to a national audience, and Fantasy Fest offered a spectacular setting in which to promote them both.

MCA Records and Buffett’s Frontline Management launched the Last Mango in Paris Cruise through a major national contest promoted on radio and through inserts included with the vinyl album. Five grand-prize winners and their guests received round-trip airfare to Key West, a sailing excursion with Buffett and a private beach party and performance on Wolkowsky’s island. The three-day trip was scheduled for October 25–27, placing the group in Key West during Fantasy Fest’s climactic weekend.

More than 75,000 entries reportedly poured in. The prize came with one more extraordinary promise: the winners and their guests would ride in the Saturday night Fantasy Fest Parade alongside Buffett and Captain Tony aboard the co-grand marshals’ custom-designed float.

Carol Shaughnessy was part of the small original Margaritaville crew assembled by Buffett and Smith. She managed the store’s fledgling mail-order operation, wrote the Coconut Telegraph newsletter and helped coordinate fan relations, including this promotion.

As Shaughnessy later wryly recalled, nothing in her job description mentioned serving paella—or hijacking a trolley.

The winners’ adventure veered off schedule almost immediately when the Margaritaville office received a call saying they were missing at the Miami airport. They were eventually located and, after a brief meet-and-greet at a hotel, boarded Buffett’s tour bus bound down the A1A for Key West. Dinner that evening was at Louie’s Backyard.

Doug Parsons was one of the lucky guests. His wife, Ruth Hauser, had been selected as one of the five winners, and more than four decades later, he still describes it as the trip of a lifetime.

“From an arrival dinner at Louie’s Backyard to our farewell lunch at the Full Moon Saloon complete with Cajun martinis, we couldn’t have scripted a more perfect Margaritaville adventure,” Parsons recalled. “It was the weekend of a lifetime.”

Along with Hauser, the winners identified by the Key West Citizen included Walker (sic) of Arlington, Virginia; John Blocker of DeLand, Florida; Bruce Lawson of Culpeper, Virginia; and Richard Pfluger of Quincy, Massachusetts.

Jimmy Buffett, center, sails with the Last Mango Cruise contest winners, their guests and members of the Margaritaville crew during their October 1985 excursion off Key West. The group was headed to David Wolkowsky’s Ballast Key for a private beach party and intimate performance by Buffett. PHOTO: HENRY DILTZ

The following morning, the winners and Margaritaville crew boarded a sailboat owned by Irwin Yachts founder Ted Irwin, remembered by at least one member of the group as “dreamy.” With Buffett and Irwin trading stories, they sailed through the waters off Key West.

Their destination was Ballast Key. Wolkowsky had long welcomed Buffett and other friends to his private island retreat, and now he was opening it to the Last Mango winners for an afternoon far removed from the Fantasy Fest crowds.

Near Wolkowsky’s rustic beach house, a massive pan of paella simmered while Shaughnessy helped serve the group. The winners relaxed beneath the shade as Buffett sat on a stool with his guitar, taking requests and playing songs from his new album.

Parsons remembers cheeseburgers, oysters, margaritas and an intimate performance by Buffett for the contest winners, their guests and the crew.

It was, in Shaughnessy’s recollection, sheer magic.

The afternoon also brought part of Buffett’s Key West journey full circle. The struggling musician Wolkowsky had once encouraged was returning as a nationally known performer, bringing contest winners to his old friend’s island to celebrate an album inspired by another of Key West’s legendary characters.

Jimmy Buffett’s tour bus, left, carried the Last Mango Cruise winners and their guests from Miami to Key West. At right, David Wolkowsky’s beach house on Ballast Key, where the group gathered for a private island party and intimate performance by Buffett. PHOTOS: RUTH HAUSER/DOUG PARSONS

Jimmy Buffett gathers with the Last Mango Cruise winners and Margaritaville crew during a private party on Ballast Key, the island retreat of his longtime friend and early patron David Wolkowsky. Buffett played an intimate acoustic concert and took requests from the group. PHOTO: HENRY DILTZ

The Parade Leaves Without Them

There was only one problem with spending a nearly perfect afternoon on a private island: nobody wanted it to end on schedule.

According to Ruth Hauser’s account, “Jimmy took a speedboat back. He was to be Grand Marshal of the Fantasy Fest Parade that night and had to get back and the fun on the island had run a little long. The rest of us took the slow ride on the sailboat.”

By the time the winners reached Duval Street, the Fantasy Fest Parade was already underway. In those days, floats staged on side streets near the southern end of Duval and joined the procession as it moved from the Atlantic toward the Gulf. Buffett and Captain Tony, surrounded by palm fronds, tropical greenery and balloons on the grand marshals’ float, were already well ahead. With Duval Street packed with revelers, the contest group had no realistic chance of catching them on foot.

The carefully planned national promotion was falling apart at the moment it was supposed to reach its grand finale.

That was when Shaughnessy spotted an open-air trolley already traveling in the parade. It was carrying the Junkanoos, Key West’s traditional Caribbean street band.

So she commandeered it.

The band welcomed the stranded visitors aboard and played as the trolley continued along the parade route. The winners never reached the grand marshals’ float, but they did make it into Fantasy Fest.

“We even got to be IN the Fantasy Fest parade. We rode on a trolley with a live reggae band! It was the weekend of a lifetime!!” Parsons wrote about the experience.

Up ahead, Jimmy Buffett and Captain Tony continued down Duval Street past thousands of spectators, apparently drinking Coors Light (who was a sponsor), snacking on Doritos and perhaps indulging in a little of Captain Tony’s finest. For the crowd lining Duval, seeing two friends whose stories had become inseparable from Key West riding together on the grand marshals’ float was about as hometown as a tribute could get.

The Last Mango Cruise winners visit Buffett’s original Margaritaville Store at Land’s End Village during Fantasy Fest weekend in 1985. The Key West store had opened less than a year earlier. PHOTO: HENRY DILTZ

Ruth’s account picks up again the following morning:

“Sunday morning the contest winners were interviewed on the veranda of our hotel by reporters from the Key West Citizen and the Miami Herald. We were treated to a ‘shoplifting spree’ at the original Margaritaville Store, had lunch with Jimmy and then went on a tour of Key West on one of the trolleys. After our final good-byes with Jimmy we were whisked from Key West to Miami on an old, rumbling DC3. It was a most appropriate ending to a once in a lifetime experience.”

In the end, the Last Mango promotion did more than sell an album. It brought the world that inspired the music to life: Captain Tony rode beside Buffett through the parade, Wolkowsky opened the island where Buffett had once found his footing, the small Margaritaville crew improvised when the plans went sideways, and 10 fans were swept into Fantasy Fest with them. The winners had come to Key West to celebrate Last Mango in Paris. By the time they left, they had become part of the same lore that inspired it.

Carol Shaughnessy finds a moment to laugh amid the controlled chaos of the 2024 Fantasy Fest Parade. Armed with her trademark clipboard, Shaughnessy spent decades directing the media stand on Duval Street, cueing and spacing each entry for the cameras. PHOTO: VIRGINIA WARK

A New Chapter in the Story

The 1985 parade was only the beginning of Carol Shaughnessy’s long Fantasy Fest history. Long after her time with Margaritaville, she joined NewmanPR in 1999 as deputy director of the Florida Keys News Bureau and spent the next 25 years sharing Key West with the world. Among her annual assignments was directing the Fantasy Fest media stand on Duval Street. Armed with the ever-present clipboard that became her trademark, she went from commandeering a trolley to get one group of Buffett fans into the parade to cueing and spacing the entire procession for the cameras, a role she continued through 2025.

Today, Shaughnessy remains part of Buffett’s Key West story through Just a Few Friends, sharing her firsthand memories through Tales from the Chart Room and helping preserve the people, places and adventures that shaped his island years.

Now, the story Shaughnessy has spent decades preserving is headed back down Duval Street. On October 24, 2026—41 years after Buffett and Captain Tony served as Fantasy Fest grand marshals—Buffett’s music will once again roll through the parade.

Caleb Hogan, creator and star of A Pirate Looks Back Jimmy Buffett Tribute Show, performs during Just a Few Friends Key West. Hogan will bring Buffett’s music to the 2026 Fantasy Fest Parade aboard “The Volcano Is Gonna Blow!” float. PHOTO: NICK DOLL.

Musical Icons and Iconic Musicals

This year’s theme, “Musical Icons and Iconic Musicals,” creates a fitting opportunity to honor the artist most closely associated with Key West. Margaritaville Cafe Key West, Just a Few Friends and Caleb Hogan from A Pirate Looks Back Jimmy Buffett Tribute Show are joining forces to create “The Volcano Is Gonna Blow!” parade entry.

Hogan will perform Buffett’s music aboard a full-scale tropical volcano float, with the Margaritaville Second Line Krewe turning the street around him into a moving celebration.

This time, the public is invited to do more than watch—and no contest win is required. Participants can join the Second Line umbrella brigade, carry banners and Jimmy Buffett memorial placards, serve as parade monitors, hand out leis or simply dance down Duval surrounded by music, bubbles and thousands of spectators.

The float will be different, and so will the faces along Duval, but the spirit remains familiar. In 1985, five contest winners and their guests came to Key West expecting a vacation with Jimmy Buffett. They left with a story they would still be telling more than 40 years later.

That is the magic of Fantasy Fest—and of Key West itself. You never quite know how the day will unfold, who will invite you along or when you might suddenly find yourself inside a story.

On October 24, there will be another chance to become part of one.

After all, the best Key West stories begin with just a few friends—and you’re invited.

Details and registration: https://events.humanitix.com/fantasyfestparaderegistration

After the parade, the celebration continues at Margaritaville Cafe Key West with Musical Icons Karaoke, sing-alongs with Caleb Hogan and drink specials for parade participants. The after-party is FREE and open to everyone—whether you marched, watched from Duval Street or simply want to join the fun. No ticket or parade registration is required.

“All events not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.”

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