Retirement the Margaritaville Way

At the active-living community for Jimmy Buffett enthusiasts, it’s five o’clock everywhere.
A beach scene with relaxed elders.
“We like the idea of being happy,” the head of the Jimmy Buffett-branded communities said of the residents’ attitude.Illustration by Nada Hayek

The first person I met at the Bar & Chill was a bald guy in a black T-shirt, black drawstring shorts, and flip-flops, with a Harley-Davidson tattoo on his right arm and a claddagh ring on his left hand. He was drinking and laughing with a few friends. He gestured to the empty stool next to him and said, “We don’t bite.”

I offered an expression of if-you-insist, and he said, “Bring it.” His tone was cheerful, as you might expect at the Bar & Chill, the principal drinking-and-dining establishment that looks out on the town center of Latitude Margaritaville, an active-living community for Jimmy Buffett enthusiasts, aged “55 and better,” in Daytona Beach, Florida. The Bar & Chill was open to the evening. A gentle breeze fanned the lanai. On a flat-screen, the Providence Friars led the Vermont Catamounts by a few buckets. A bartender brought a Perfect Margarita in a plastic cup.

The bald man, drinking a vodka soda, said his name was Phil. Phil Murphy, from Arlington, Massachusetts, aged sixty-four. Formerly a research director at Forrester, retired since 2015. “I was in the air for twenty years,” he said. He looked and sounded less like my idea of a Parrothead, as Jimmy Buffett’s diehard fans are called, than like Mike Ehrmantraut, the melancholic fixer in “Breaking Bad.” Standing off his left shoulder, his wife, Betty, red hair cut short, added a dash of urbanity, a spritz of Allison Janney. Phil and Betty had organized an emergency fund for the restaurant’s staff during its Covid shutdown. One of their friends declared them “the king and queen of the Bar & Chill.”

“True story,” Murphy said. “We read about Latitude Margaritaville. It was 2019. April-ish. I said, ‘Oh, my God, this fucking place is going to be awful. All these people with parrots on their heads. Jimmy Buffett playing twenty-four hours a day.’ We thought, Let’s go look, as a goof.”

At the time, the Murphys had retired to a third-floor oceanfront condo down the coast, in Melbourne Beach: the perfect forever home. “We gutted it and did it up like we were going to die there,” he said. They walked up and down the beach every day, but even a beach can get old. “In four years, we made four friends. Everyone was a part-timer. So we did some retirement math. We assessed the carrying costs.” The math, and a yearning for friends, told the Murphys to move to Margaritaville.

They were early adopters but not true pioneers. In November, 2017, more than a hundred and fifty prospective buyers had camped out overnight in the parking lot of the sales center, in anticipation of opening day for down payments. The parking-lot scene was on brand: it had a festival air, with tents, a steel-drum band, food trucks, and stacks of pizzas. A movie played on a giant screen: “Jurassic World,” in which Buffett has a cameo as a bartender rescuing a couple of margaritas from an outdoor table before some pterosaurs swoop in. Strangers befriended one another and decided, overnight, to become next-door neighbors.

“We left oceanfront to come here,” Murphy went on. The base cost for their Latitude Margaritaville house—of a configuration called the Breeze, from the Beach Collection of options, with three bedrooms, three bathrooms, and a two-car garage—was three hundred and thirty thousand dollars. The extras—tile floors, chef’s kitchen—ran them another hundred thousand. “It’s done,” Murphy said. “It’s nice.”

A swim class at Latitude Margaritaville.Photograph by Tobias Hutzler for The New Yorker

The housing stock, a range of villas and cottages, is, by today’s standards, compact and tasteful—single-story buildings with sensible layouts and patios that, typically screened in, can look like aviaries. People covet three-car garages, for their golf carts and motorcycles—there are a lot of both in Margaritaville—but most have two-car garages. A popular indulgence is eight-foot-tall interior doors. Tracts of development radiate out from the town center, where, in addition to the Bar & Chill and the sprawling puzzle-piece-shaped Paradise Pool, with palms, cabanas, and tiki huts, there is the Fins Up! fitness center, the Last Mango theatre and banquet hall, and an outdoor band shell and plaza, with a movie screen, for concerts, Sunday N.F.L. games, and such. There is also a beach club on the coast, in Ormond-by-the-Sea, twenty minutes away by shuttle van, with pool, bar, and cabana set into the dunes, on the former site of a run-down motel, across from Hanky Panky’s Lounge. “Glory Days” on the speakers, bull sharks in the sea.

At the Bar & Chill, and everywhere on the grounds, light classic rock plays all day. You hear it in the village square, in the locker room at the gym, in the model villas that have been staged with plastic cheeseburgers and plastic margaritas. Sometimes it’s Jimmy Buffett songs, sometimes it’s something else. At that moment, it was Steely Dan, “My Old School”—“I remember the thirty-five sweet goodbyes.” Murphy wasn’t actually a Parrothead, he said. He preferred Bonnie Raitt, Little Feat, Stevie Ray Vaughan. “But do I like some of Jimmy’s music? Yes, I do. I had a brother, Dave, who died on July 11, 1988. He was forty-eight. Congenital heart disease. He was working on the space shuttle for Siemens. He was a Jimmy Buffett fan. My mother wrote to Jimmy. To thank him for the music. Jimmy wrote her back. He wrote her back! I eulogized my brother with the lyrics from the song ‘The Captain and the Kid.’ You know it?”

I didn’t. Murphy was now crying. He turned away to collect himself. Changes in attitude. After a few moments, he apologized and introduced me to his friends. One of them was his neighbor from across the street in what was known as Phase 2—the second neighborhood to have been built. (Phase 5, consisting of six hundred and forty-one homes, is now fully developed, and half sold, and lots are for sale in Phase 6. There is room and approval for nearly four thousand homes.) The neighbor was Jack Sjursen, a retired ironworker from Patchogue, on Long Island, who was turning sixty-two the next day. “It’s my birthday, bitch!” he called out. He appeared to have momentum. He’d also just learned that he had a new grandson, and was going saltwater fishing at dawn. “I fish and I golf,” he said. “I’ve been here for two and a half years, loving every minute of it.”

The citizens of Latitude Margaritaville testify so consistently to a life of gratification that one suspects, but finds no evidence for, a regimen of happy pills or talking points. Disgruntlement and curmudgeonliness must exist, but not in view of a visitor susceptible to such traits.

“My husband doesn’t own pants.”

“We’ve got four bars in our villa.”

“The freshman fifteen is real here.”

Stuart Schultz, a former summer-camp director who, as Latitude Margaritaville’s head of residential community relations, serves as a kind of cheerleading pooh-bah, told me, “It’s like being in college, but with money and without having to study. You have a great dorm room, you never have to go to class, and there’s always a party.”

One resident said, “In our previous life, we could do paper calendars. Here we had to learn Google Calendar.” Some had college- or adult-aged children living with them who were startled by their parents’ social lives. “My daughter’s always, like, ‘You’re going out again?’ ” one woman said. Men with guitars set up outside someone’s garage, and the golf carts appear out of nowhere. Commence the beer pong. Pool parties, poker nights, talent shows, toga parties, pig roasts. Cigar-club meeting, group renewal of wedding vows, a pub crawl in old St. Augustine. Oktoberfest this fall had a “Gilligan’s Island” theme; “Hoodstock” was hippies, Fireball, and multicolored jello shots. The golf carts zip and swerve. “By the time we got to Phase 3, we were driving on people’s lawns!” one participant told me. (“Open containers are encouraged,” he said.) An Andrea Bocelli concert in Orlando, or a pajama party at the Last Mango, with a screening of “The Polar Express.” Proximity to Port Canaveral means easy cruise-ship access; the residents set sail, often in big groups, on vacations from their permanent vacation. A couple of hundred of them were booked on a cruise to Bermuda this spring.

If it’s isolation that ails us—our suburban remove, our reliance on cars, our dwindling circles of friends, our lack of congregation and integration and mutual understanding, of the kind described by Robert Putnam in “Bowling Alone”—then the solution, especially for those tilting into their lonelier elderly years, would seem to be fellowship, activity, fun. In the Margaritaville calculus, the benefits of good company outweigh the deleterious effects of alcohol. Merriment is medicinal.

At a happy hour one night, I met Chuck and Christina Danner. Chuck, fifty-eight, was ex-military intelligence, now in electronic payments, as yet unretired. Christina, fifty-four, had worked in payments, which is where they’d met: this was, for both of them, a second marriage. (An underage resident, upon turning fifty-five, might have a “Finally Legal” party.) Originally from Pennsylvania, they’d moved to Daytona from Denver, and owned a Harley, two Jeeps, and an R.V. They were among the first fifty people to arrive at Latitude Margaritaville.

One of the many resident bands.Photograph by Tobias Hutzler for The New Yorker

Chuck told me, “If you don’t get here and automatically relax and think, This is great, there’s something wrong with you, and you don’t belong here.”

When Chuck was fifty-one, he had a heart attack. “I nearly died,” he said. “The E.M.T.s beat the shit out of me.” Recently, he’d been to see his cardiologist, who reported that all his vitals were almost shockingly strong: “He said, ‘I’d never be able to tell that you ever had a heart attack.’ ” Chuck chalked it up to the Margaritaville life style and outlook. Another resident at the happy hour chimed in: “My cardiologist told me, ‘I’m from New Orleans. I’m on call all the time down there at Latitude Margaritaville, and they throw it down pretty hard!’ ”

The chief executive of Margaritaville Holdings, the parent company of Latitude Margaritaville, is a New Yorker named John Cohlan. In 1994, Cohlan was an associate at Triarc, the investment firm co-founded by Nelson Peltz, which owned RC Cola and Arby’s. That year, Peltz moved the firm temporarily to Palm Beach. Cohlan, thirty-six and single at the time, didn’t know anyone there; a friend introduced him to Jane Slagsvol, Jimmy’s wife, and, eventually, Cohlan met Buffett himself. At Jazz Fest, in New Orleans, he saw the enthusiasm of Buffett’s fans during his set and had an epiphany that Buffett might be a more substantial and self-sustaining brand than any that Triarc owned. “He was a real businessman!” Buffett told me recently. Buffett had already, as he put it, “opened that vein of the mine” with a Margaritaville bar and a T-shirt shop in Key West. Disney had shown interest in a partnership but hadn’t agreed to Buffett’s terms. The investor Warren Buffett, whom Jimmy had got to know after a Buffett-clan pilgrimage to a South Pacific island populated by Buffetts (a DNA test revealed no blood relation between the two), had advised him, Ask for what you want, and if they say no someone else will come along. Uncle Warren, as Buffett calls him, was right. That someone was Universal Studios. Buffett enlisted Cohlan to help him establish a twenty-thousand-square-foot Margaritaville restaurant at the entrance to Universal’s Islands of Adventure theme park in Orlando. Cohlan also outflanked Seagram, which owned both the park and Buffett’s record label, on the question of what alcohol to stock—with Seagram, Margaritaville created its own. Buffett brought in Cohlan as his partner, saying, “I can’t pay you what you’re making on Wall Street, but you get to come to work in shorts and flip-flops.”

More than twenty million people a year pass through the doors of a Margaritaville-branded establishment. The company, with annual system-wide sales of $1.7 billion, licenses the name to restaurants, hotels, casinos, and resorts, and sells a wide array of branded merchandise: umbrellas, towels, beach furniture, bicycles, blenders, frozen shrimp, and Key-lime-pie mix. It recently announced plans to launch a cruise line. (Before that, Buffett himself had never been on a cruise ship.) Given the age of Buffett’s fan base, and the life style he’s hawking—as well as baby-boomer demographics—the move into active living was a natural one.

“Who knew people wanted to live in Margaritaville?” Buffett told me. “I thought for a while it was a myth.”

The development in Daytona was a joint project of Margaritaville Holdings and Minto Communities USA, the American branch of a builder based in Ottawa. In 2017, Minto had bought roughly two thousand acres of brush and swamp, about seven miles from the coast, across the street from the Ladies Professional Golf Association’s headquarters and its pair of signature courses. Minto had a plan to develop a retirement community there called Oasis. Cohlan caught wind of it, and Oasis became Latitude Margaritaville, taking its name from Buffett’s breakthrough 1977 album, “Changes in Latitudes, Changes in Attitudes”—the one with the “Margaritaville” single. The latitude would be east-central Florida, or any place where it doesn’t ice over in winter; the attitude would be strummin’ the six-string on a front-porch swing. The partners developed a nearly identical one in Hilton Head, South Carolina, and last year launched the biggest one yet, in Panama City, Florida.

“We were getting polarized as a country politically, and then the pandemic comes along,” Buffett said. “It’s a good place to be if you like your neighbor.”

Cohlan told me, “It attracts people—and this may sound corny—who have a set of common values. Those values are rooted in this attitude. A person created that attitude. But whether or not you feel connected to that person, it’s not physics. It’s, ‘We’re interested in meeting other people. We like to have fun. We don’t want to be overly political. We like the idea of being happy.’ ”

After my night with Phil Murphy at the Bar & Chill, I looked up “The Captain and the Kid.” It was on “Down to Earth,” Buffett’s first album, from 1970, which never really got off the ground. He wrote the song about the death of his grandfather, a ship captain who’d instilled in Buffett a love of the sea when he was growing up, on the Gulf Coast of Alabama. Buffett says that the record company wanted him to change the ending, to make the song less sad, but he refused:

We both were growin’ older then and
Wiser with the years
That’s when I came to understand
The course his heart still steers
He died about a month ago
While winter filled the air
And though I cried, I was so proud
To love a man so rare.

It is impressive, in that American way, how Buffett steered from there to here—from struggling singer-songwriter whom no one ever called the next Bob Dylan to surefire arena act and hospitality conglomerateur. A poor man’s Gordon Lightfoot grows into a drinking man’s Martha Stewart, hardly having to change his tune.

Nashville, on that first go-round, anyway, didn’t work out for him. His second record, “High Cumberland Jubilee,” a string-band gambit without a whiff of brine, didn’t get released. He had an infectious personality, a facility with words, and some mojo as a solo performer, but the charisma didn’t translate onto vinyl, or onto the charts. For a while, to make ends meet, he worked as a reporter at Billboard. Humbled and frustrated, he retreated, in 1971, to Key West, at that time a redoubt of leathery sots and acid freaks, drug smugglers, treasure hunters, and shrimpers, along with artists and writers who weren’t necessarily not one or two of those other things. Key West became material and muse. Buffett signed on as second mate on a fishing charter (“I kind of had it made”) and played for drinks and tips at the Chart Room, Capt. Tony’s, and Crazy Ophelia’s. Among his acquaintances were the writers Jim Harrison and Thomas McGuane, whom Buffett called Captain Berserko. (McGuane eventually married Buffett’s sister.) Periodically, he left the Keys to perform around the country, honing his emergent Caribbean cowboy style—“trop rock,” or “Gulf and Western”—and an audience took root. Still, it was a hard road. As Ryan White chronicles in an unauthorized biography, “Jimmy Buffett: A Good Life All the Way,” from 2017, Buffett was on the verge of buying a Boston Whaler to join the local marijuana-smuggling game, but, after a successful gig on the undercard at Max’s Kansas City in New York, he managed to sell a third album, “A White Sport Coat and a Pink Crustacean.” The liner notes, by McGuane, burnished the emergence of a revised persona: A “throwback altar boy of Mobile, Alabama, brings spacey up-country tunes strewn with forgotten crab traps, chemical daydreams, Confederate memories, Ipana vulgarity, ukulele madness and, yes, Larry, a certain sweetness.”

“Margaritaville” was his first big hit, peaking at No. 8 on the Billboard chart in 1977. He has said he wrote it in six minutes, the first half of those in a notebook after an afternoon of drinking margaritas at a bar in Austin, Texas, the rest in a traffic jam on the Seven Mile Bridge, on returning to Key West. It was a catchy and clever distillation of the happy-derelict attitude, the celebration of leisure, transgression, and good humor that he’d been describing in song and projecting onstage for years.

At Latitude Margaritaville, the pickleball courts are typically busier than the tennis courts.Photograph by Tobias Hutzler for The New Yorker

I was eight when “Margaritaville” played over and over on the AM dial—in the summer not only of Sam but of Barry Manilow and Andy Gibb. It’s easy to disdain it now, but I associated its steel-drum calypso sound and droll delivery with the good life. I had a great-aunt, Julie, who each Christmas gave me a vinyl LP, relying on the recommendations of the record-store clerks. One year, she gave me “Anthology,” a compilation of the Band’s greatest hits. Another year, it was a Herb Alpert release called “Rise.” One wonders how she was describing me to the clerks. In 1980, it was “Volcano,” by Jimmy Buffett.

It was obvious even to an eleven-year-old that the album wasn’t in any way hip. The cover, with lettering in flamingo pink, was a garish painting in green and aquamarine of a Caribbean island—Montserrat, where Buffett had recorded it. The music was adept but soft. I learned the lyrics, as one used to, sitting with the sleeve in hand and a full batch of brain cells between the ears.

Over time, Buffett has come to be admired and complimented by an array of real aces, among them the late Allen Toussaint (who wrote a song about Buffett’s good vibes) and even Dylan himself, who once, when asked to name his favorite songwriters, chose Buffett. A Zimmy jest? Perhaps. But Dylan has covered Buffett live. Still, awards and critical acclaim have mostly eluded him, and one can detect in his recitations of his ascent to cultural iconhood, self-deprecating as such accounts are, the lightly worn shoulder chip of a self-made titan.

In the late eighties, Buffett expanded into book-writing. He has published seven works of fiction and nonfiction and is one of just a handful of authors to be No. 1 on both best-seller lists, along with Styron, Hemingway, Steinbeck, Dr. Seuss, Irving Wallace, and Mitch Albom. In his books and songs, his world view metastasized into something akin to an empire of attitude, a Margaritaville of the mind and of the travel brochure. The broader idea of Margaritaville has itself drifted over time to encompass commercial horizons that have little to do with the man or even the song. Buffett is now, if not a billionaire, then at least a half of one, with houses all over the place, and boats and planes, and high-powered friends and harried assistants who keep his schedule and ward off entanglements. (“Fins up!” is the universal sign-off among Margaritaville employees.) He turned seventy-five on Christmas Day and still surfs, sails, fishes, and flies planes, and occasionally pops up before an open mike to charm a happy-hour crowd. One thing he isn’t doing is wasting away.

On my first morning in Latitude Margaritaville, I had a slot in an exercise class. When I arrived at the fitness center, a trainer named Todd was leading seven women through suitcase lunges as George Harrison sang “Got My Mind Set on You.” Some of these women had, a few nights before, put on a dance performance during a talent show in the new theatre, doing numbers from “All That Jazz” for their fellow-residents. I was sorry to have missed it.

“Is this Butts and Guts?” I asked Todd, during a lull.

“Actually, this is Body Blast,” he said. “But we do work our butts and guts!”

Butts and Guts came next. Patrice Ambuter, the instructor, wore a headset with a microphone and had powerful arms and shoulders. She asked us to assemble an arsenal of implements—exercise ball, step-up board, yoga mat, hand weights, stretchy bands, various slidey things—and then pair up. My partner was Doreen Asselin, a retired administrative assistant from a V.A. hospital in Bedford, Massachusetts. “You picked the hardest class,” she said.

Ambuter got us started with “Fresh,” by Kool & the Gang. Fresh, indeed. At fifty-two, I was the youngest in the room by at least a decade. (The average age at Latitude Margaritaville is sixty-four.) And yet, for the next hour, at a pace and with an intensity one might associate with the seven-minute workout, the session demolished me. Ambuter inevitably noticed my attempts to cut corners and made the others do extra reps until I’d done mine right. Afterward, I hobbled to the showers, as Buffett, in some recorded concert patter playing over the gym speakers, led an audience through his customary “land shark” intro to his hit song “Fins.” The Parrotheads clasp their hands together over their heads, in imitation of a shark fin, and swerve left and right. “This counts as going to the gym tomorrow,” Buffett said onstage.

By the following morning, my glutes and hip flexors had tightened up. But I had a date to play pickleball, an adaptation of tennis that has skyrocketed in popularity, especially among seniors. There are ten courts, and they are always busier than the five tennis courts. (The absence of golf on the premises distinguishes Latitude Margaritaville. A retirement community without golf is one with more land for houses—and fewer golfers.)

My partners were among Latitude Margaritaville’s top players: Allen Farkas, a retired pharmaceutical salesman originally from Canarsie, Brooklyn; Al Bobst, a retired chief master sergeant from the Air Force; and Hershey McChesney, a retired teacher and school administrator from Southern California. I had never played, but I can get around a court O.K., and we had a series of spirited games in the mounting heat, with some light hazing of the new kid.

Afterward, we sat in the shade and watered up. Bobst, seventy, from Spokane, had served in Desert Storm, and had been a survival instructor, specializing in “personnel recovery.” “We were the guys who interrogate and torture,” he said. He was joking. I think.

“Who knew people wanted to live in Margaritaville?” Jimmy Buffett said.Photograph by Tobias Hutzler for The New Yorker

Farkas, sixty-two, had been buyer No. 61. “I was the idiot who slept in the parking lot,” he said. “My wife gave me a list of lots she liked.” He’d lived in Florida for forty years. He sounded like Brooklyn, but he bled Miami Dolphins turquoise. Everyone in Latitude Margaritaville got around on golf carts, many of which were customized. (Rock Rotundo, the owner of Ace of Carts, one of Florida’s biggest cart dealerships, owns a home in the community.) Many had Parrothead motifs, but Farkas’s was decked out in Dolphins regalia; he’d named his bulldog Csonka.

“This is by far the greatest place I’ve ever lived,” Farkas said. “Ninety-nine per cent of the people here are wonderful. The one per cent you don’t deal with. They’d bitch and fucking moan wherever they lived. You can find miserable people everywhere. If you can’t be happy here, you can’t be happy anywhere.”

The big gorilla of retirement living is the Villages, seventy miles west, America’s fastest-growing metro area. It has fifty-six golf courses and some seventy thousand homes—and a reputation, backed up by the ballot box, as a stronghold of Trumpism. “That’s where our parents live,” Farkas said.

Several people told me that it is considered bad form to talk about politics in Margaritaville. “Many people here strive for no politics,” Murphy had said. “All you have to do is look at the fucking Villages. Leave it at the front gate, you douchebag.” During the 2020 election, this standard was tested. The residents eventually passed an ordinance against lawn signage. Still, I encountered a range of opinions about the current President and his predecessor. There was at least one golf cart flying the blue-line American flag, in support of the police. Some rolled their eyes when it passed; others waved.

McChesney had customized his golf cart with the tools of his trade, or rather of his hobbies. He had a built-in rack that held a pair of cornhole boards, and a quiver of tools for the wrangling of reptiles. He had majored in biology and is the community’s self-appointed wildlife expert. He hands out business cards for “Hershman’s Reptile Re-Homing Service” and takes regular phone calls from residents asking him to remove alligators, turtles, and snakes from lawns and driveways. To comply with environmental regulations, Latitude Margaritaville left undeveloped some patches of thicket and swamp, from which critters occasionally wander, and to which McChesney returns them.

McChesney is sixty-five. He has a mustache and a soul patch and a tattoo of a shark on one calf and one of a hula girl on his right biceps, with the name of his wife, Terry, underneath. (A sign on the back of their golf cart reads “The Hershman & his Hula Girl.” Terry is fifty-seven. She won the costume contest at a Grinch-themed pre-Christmas block party, an all-day affair for some six hundred residents. McChesney told me, “She looked hot, real hot,” and sent me a photo of Terry in a Santa’s-elf getup.)

McChesney’s father had been a drill instructor based at Camp Pendleton, outside San Diego. Seeing the penguin exhibit at SeaWorld persuaded McChesney that he wanted to be a marine biologist. At San Diego State, for his senior project, he tried to align biological and geological eras. “Turned out, that time line doesn’t work. They were, like, ‘Are you a creationist?’ ” he said. He became a teacher instead, and spent more than thirty years at a middle school in the San Bernardino inner city, then a few more as a school administrator. He and Terry had been searching for a place to retire, with Terry, especially, insisting on a tropical town, maybe in Central America or the Caribbean. “But every home we looked at had bars on the windows,” she said.

One day, at work, a colleague told McChesney about Latitude Margaritaville. “I closed the door and cancelled all my appointments and looked it up. When I got home, I said, ‘Hey, honey, check this out.’ And she said, ‘Don’t show me unless you mean it.’ ” A few weeks later, they’d bought a lot, sight unseen. Phase 2, on Jollymon Way.

Late in the day, I found McChesney playing cornhole in the village square with some friends. I joined in for a while, and then we loaded up the cornhole boards and got into his golf cart and, beers in hand, hummed down the cart path, in the pink subtropical twilight, pines and palms whizzing by, a whiff of fry grease lingering in the air.

Every Thursday, McChesney and a bunch of the pickleball boys meet up for happy hour in a nearby strip mall, at a shop called Oil & Vinegar, which has a little bar in back. This ritual is a vestige of an earlier one, called Tiki Thursdays, when the first residents, in the absence of any amenities or communal structures, held an unsanctioned B.Y.O. party every week in the tiki hut by the street of model homes. The community’s lean early months, when the new residents had little but one another for entertainment, are now deep lore, and something of a case study in the power of fellowship and the human urge to alleviate boredom.

The mall, dominated by a Publix supermarket, had been built by Minto as a complement to Latitude Margaritaville. The golf-cart-parking area was in front of the liquor store. “I don’t think it’s an accident,” McChesney said. Inside Oil & Vinegar, eight guys were drinking beer. There was talk of orthopedic implants, the advantages of cinder-block construction (it deters termites), and the cabling of roofs to slabs (it keeps roofs from flying off in hurricanes).

After a while, McChesney ordered a roadie, and we cruised back to the village square, where he was due to run the third meeting of the newly created Pickleball Club, of which he was the president. On the way there, he filled me in on some of the pickle politics. Apparently, a woman named Arlene Weinstein, whom he referred to as Sweet Arlene, had been making noise on behalf of beginners about how the better players were hogging the courts. The top players didn’t want to mix with players well below their level; the beginners resented the emergence of a class system.

“Of course, he can’t walk or talk or lift his head. Still, there are flashes of brilliance.”
Cartoon by Barbara Smaller

The meeting was held in one of the community’s rec rooms. We rolled in late, McChesney looking presidential in a Harley-Davidson tank top and flip-flops, Solo cup in hand. He called the meeting to order. There were several dozen members facing four officers. I sat in back with Allen Farkas and his old Canarsie buddy Tommy Leung.

Sweet Arlene, it turned out, was the head of the social committee. “I love my committee,” she said. “Our group has a lot of good ideas.” One was a pickleball dance party.

“Remember to drink responsibly,” McChesney said.

“I’ll try not to make my jello shots too strong,” she replied.

Farkas muttered to me, “We go from the pickleball meeting to the A.A. meeting.”

McChesney gently reminded Weinstein that the committee needed approval from the officers to implement such plans. His sunny, deflective approach to enforcing a chain of command suggested the influence of his years as an administrator in the California public-school system, and of his half-finished pint of pale ale.

There was talk of updating signage and of purchasing a wind sock, and then an officer to McChesney’s right said he had a few remarks to make about court etiquette. The room got noisy, as a discussion kicked up, and the officer called out, “I’m not done with etiquette yet.” Order restored, he spelled out the proper way to return balls that have rolled onto adjacent courts.

There was a quality of pleasure, even patience, in the way everyone kicked back and worked almost playfully through the thorny issues of the day. It was the first meeting I’d been to in years where I didn’t get the sense that the participants wished they were somewhere else. Still, there were back-row clowns. At one point, Farkas laughed at something on his phone, and, a moment later, texted me a mildly lewd meme.

Afterward, McChesney, Farkas, Leung, and a few others hit the Bar & Chill. Apparently, some of the wives were playing mah-jongg. “The women love the social part,” one of the men said, as a half-dozen men gathered around a table.

“I’m not handy at all, but, if something needs fixing, in thirty minutes I can have six guys over to help me,” Farkas told me. And one had to admit that, in the communities they’d come from, where neighbors kept to themselves and had redundant skills, this would not have been so. A point that residents kept making to me was the diversity of people, of backgrounds and talents. Chuck Danner likened the place to his men’s-league hockey team back in Pennsylvania, for the mix of blue- and white-collar guys. It was like a hockey team in other ways, too: I saw hardly any people of color at Latitude Margaritaville.

Putting aside the plumbers, carpenters, and electricians next door, and the real-estate agents and snake wranglers, there were several rock bands’ worth of musicians, a few generous oenophiles, and even a go-to source for wild game. Earl (the Pearl) Snyder, a former professional bodybuilder in a Pittsburgh Penguins jersey, strode up to the table and mentioned that he had recently made a batch of venison jerky, seasoned with fennel and liquid smoke, if anyone wanted some. He also had elk meat. He said he’d just shot a nine-point elk in New Mexico with a rifle, from three hundred and twenty-five yards. “It was bleeding out on the fourth shot,” he said. “The guides paid an Indian kid to haul the elk out.”

One day, I had a late-afternoon beer on the patio outside the Bar & Chill with four retired first responders, who had stories to tell about their traumatic experiences during the terrorist attacks of September 11, 2001. The anniversary is a rare solemn occasion at Latitude Margaritaville—there’s a ceremony in the village square, where a resident, a retired N.Y.P.D. bagpiper, plays “Amazing Grace.” “The month of September, we practically sit shiva,” one of the officers said. Andy and Marta, sixty-two and fifty-two, who are married, had been with the Washington, D.C., airport police. Mickey, sixty-six, who was an N.Y.P.D. detective, had been dispatched on 9/11 to New Jersey to chase down an alleged terrorist bomber. Pete, sixty-six, a cop with the Port Authority of New York and New Jersey, had gone to Yankee Stadium the night of September 10th for a game that never got started, owing to foul weather. He wound up getting drunk at a bar in Manhattan, then, to his wife’s dismay, driving home to Jersey City. He called in sick. More than half of the officers in his squad died that day. “You don’t get over that,” he said, with tears streaming from beneath his sunglasses.

“In lieu of barking, he recorded a sweet diss track about you.”
Cartoon by Jeremy Nguyen

They’d sold their homes and come south, in large part, they said, because of the high taxes in New York, New Jersey, and Maryland. This was a near-universal refrain. Low taxes, low homeowner’s-association fees, warm climate, like-minded folk: you can’t knock it. In one sense, it was heartening that men and women who’d put their life on the line had got a chance to live out their next chapter in a place like Margaritaville. But I couldn’t help thinking, home-town-centrically, of all the retired public-sector employees I’d met in Latitude Margaritaville from high-tax blue states who’d got their pensions, which were funded (or underfunded) by those high taxes, and had withdrawn to this low-tax red state. It wasn’t just one-per-centers who were fleeing to Florida to escape the state and city tax regimens of the Northeast. Our ramshackle system of interstate tax arbitrage had provided incentives for teachers, bureaucrats, health workers, firefighters, and police officers to exacerbate both the exodus and, perversely, the burden on the taxpayers left behind. Whatever one’s politics, it wasn’t hard to see Latitude Margaritaville as a manifestation of an economy out of whack. The excesses and segregations of the Jupiter Island and Mar-a-Lago sets were one symptom of misalignment; here, less conspicuously, was another. Latitude Margaritaville came off both as an escape from America and as the most quintessentially American setting of all.

This is good business, of course. At Daytona and Hilton Head, demand for homes has outstripped supply. The parking-lot party on Night One set the script. Each cluster of new lots—each phase—sells out, making the resale market robust.

Kelley Sarantis, Latitude Margaritaville’s top real-estate agent and buyer No. 9 in Daytona, is from Massapequa, on Long Island—her father had a forklift business, in Queens, before moving down to Fort Lauderdale for a second career as a yacht broker. Sarantis worked in real estate in South Florida for almost thirty years, the last five for an old-line firm called Bob Hodges and Sons Realty. “I sold homes in Century Village,” she said, referring to another fifty-five-plus gated community. “It’s depressing. It’s like people were just going there to be warm and die.” When she and her husband, a retired Fort Lauderdale cop, moved to Latitude Margaritaville, she stayed on the Bob Hodges payroll and began handling sales and resales. If she walks into the sales office with a buyer, she gets a commission of three per cent. She has five residents working for her as agents. In 2021, there were sixty-five resales in the Daytona Latitude Margaritaville. “I did seventy-five per cent of them,” she said. “I get five calls a day. I would have never imagined it would be like this. It blows me away.” The least expensive resale, of an attached villa called the Nevis, was five hundred and sixty-five thousand dollars, up from three hundred and fifteen thousand. By the end of 2021, resale prices were thirty to fifty per cent higher than the original sale price. You might say that Margaritaville is Bitcoin for boomers.

Even Buffett himself has a house: a Bimini model. He’d visited Latitude Margaritaville at Daytona four times, Sarantis said. “One day, he came to my house,” she added. “He’d bought a house and wanted to meet the residents. He literally knocked on my door. ‘Hi, neighbor.’ Are you kidding me? I have yellow Labs. He was showing me pictures of his dogs.”

At dawn, I was on the road to Panama City, Florida, some three hundred and fifty miles west along the panhandle. Minto was building its third Latitude Margaritaville there, on a hundred and ten thousand acres of pineland in an area called Watersound, five miles from the Gulf Coast. The owner of the land, and the third partner in the project, was the St. Joe Company, a timber barony turned real-estate developer—and one of Florida’s biggest landholders. The partners had got approval to build as many as a hundred and seventy thousand homes, which would make it the largest private community in the country.

A small city out of nothing: it’s hard not to think of the subprime housing collapse of a decade and a half ago, especially as we’re many years into another asset bubble that may or may not be bursting. For now, the developers have committed to building just thirty-five hundred homes, which, though still a lot of Margaritaville, doesn’t quite trigger the same visions of foreclosure and abandonment in Florida (and elsewhere) as in 2008. Sarantis, however, thinks that Latitude Margaritaville is not as vulnerable to a downturn or a recession as the market in general. “In 2008, I saw how the Villages was only narrowly affected,” she said. “I didn’t see the values go down. If the residents didn’t need to sell, they didn’t. We have mostly cash buyers here. This is why I’m not expecting a big jolt to this community.”

When I arrived in Panama City, a hard mist was billowing in off the Gulf. The region, the Emerald Coast, is famous for its powdery white sand and green water, but on this afternoon it was all duns and grays. The stores, bars, and hotels had a bedraggled appearance that got me trying to remember the names of the season’s tropical storms. The Watersound site was about five miles north, on Route 79, past Wild Thang Airboat Tours, and just short of the Southern Hay Company Feed & Supply depot and the Laguna Beach Christian Retreat. The sales center for Latitude Watersound, as it is called, was on a corner across from a vast clear-cut expanse that was destined to be a shopping center. The density of a Latitude Margaritaville supports commercial growth, which encourages more development. A standard line at the Bar & Chill was that Daytona Beach, by reputation a run-down town occasionally saturated with bikers, spring breakers, and Nascar fans, was coming up in the world, and that the revival owed a lot to Margaritaville.

Because of the weather by the Gulf, and the rawness of new construction in this stretch of sand and mud hacked out of the pines, the site didn’t feel like anyone’s idea of paradise, but inside the sales center an immaculate Florida Keys-cum-offshore-bank aesthetic prevailed. It was nearly identical to the one in Daytona. Pastels, potted palms, murals of beaches and hammocks, displays of Margaritaville products, smiling faces. A signature fragrance—evocative (to me, anyway) of sand, coral, and skittering lizards—was being piped in.

That evening, a few dozen of the Latitude Watersound pioneers—several of whom had moved in already, the rest of whom were awaiting the completion of construction—gathered for some happy-hour hang time at the Margaritaville restaurant in Panama City. There was as yet no place to congregate at the Watersound site. They had an upstairs loft space to themselves, beneath a fake palm tree and a life-size model, hung from the rafters, of Buffett’s seaplane Hemisphere Dancer, which was forever flying toward a giant mural of a partly cloudy sunset sky. The ceiling was painted with a vast pirate-style map of the Caribbean. Cocktails arrived, with platters of nachos and wings. Everyone had already got to know one another, even prior to moving in. “We all party together,” one woman said. “We already know a hundred people.” Many of the men were retired members of the armed forces, the panhandle and its environs having a high concentration of military bases. I met a teacher, a college-admissions administrator, an air-traffic controller, a firefighter, a corrections officer. Some had missed out on Daytona; others had been coming to this stretch of coast for years, or even already owned a condo on the beach, but, like their counterparts in Daytona, had chosen to retreat inland to be among like-minded extroverts. They still staked a claim to the shore, however. The thought of Daytona’s orange beaches caused a few to grimace. This was the place, even if it wasn’t.

At one point, “Margaritaville” came over the bar’s stereo, and everyone perked up, dutifully intoning the standard Parrothead chant after the line “searching for my lost shaker of salt”—“Salt! Salt! Salt!”—in a way that was at once, or maybe variously, sincere, joyful, dutiful, and abashed. I can’t say that I didn’t mutter along, too. Once you hear it, you can’t not.

Twenty-eight-plus hours later, I was in Orlando, hearing it again, in a sold-out basketball arena. Jimmy Buffett and the Coral Reefer Band were performing in front of some twenty thousand fans.

Two busloads of residents had come down from Daytona for the gig, under the supervision of Stuart Schultz, who entertained his charges with trivia games and a Margaritaville history lesson. Before the show, the Latitudeners assembled outside the arena to pre-game at the Big Storm Brewing Company.

“I did all the taxidermy myself.”
Cartoon by Zachary Kanin

The Daytona Latitude Margaritaville had got an allotment of about a hundred tickets, which were distributed to residents, at face value, by lottery. Some had procured tickets on their own. Chuck and Christina Danner had paid twelve hundred dollars for a pair in the second row. They called me over to their table outside, where they and some friends were working through a stand of tall boys. I was introduced to Rich, a former sailing and swimming coach at Rollins College, and to Ruth and Dale, who’d met as teen-agers but started dating at Latitude Margaritaville, and to Kimberly, a pilot for JetBlue.

“This is our life all the time!” Christina said. “Every day is a good day, every day is a vacation.”

Buffett later told me that, one night in the Parrothead mecca of Cincinnati, he realized that this scene—the costumes, the booze, the performative exuberance—was another kind of Mardi Gras: he was on a parade float, throwing candy. “I thought, Everybody needs it. That pure part of us that needs to have a little fun, no matter where you are. I was brought up to think that fun was the essence of life. So I was just passing it on. That’s really the nucleus of the whole thing, my coming out of that Creole culture and taking it with me wherever I went.”

Christina was dressed in a red elf costume, having come straight from the Grinch block party up in Daytona. I’d heard many refer, facetiously or not, to their costume closets, and the concertgoers had dug into theirs.

We were soon joined by a Nancy and a Rhonda, who was wearing a parrot on her head.

“Are you Phase 2?” Rhonda asked me.

I said I was no phase at all, being much too young—a remark that went from sincere to flirtatious before it was made.

Rhonda didn’t believe it. “You weren’t in the pool doing stuff?”

“I don’t think so.”

Before I went to Florida, I had thoughtlessly anticipated a convocation of fogies, or at least of people more of my parents’ generation, within range of eighty, or even that of my grandparents, a few of whom I saw wither away years ago at well-appointed but thoroughly depressing old-age enclaves outside of Philadelphia. But many if not most of the people I met in Daytona felt more like peers than elders—at least according to my ever-expanding delineation of my cohort. Here was a world of people a little older than I who had reached a stage of life that I hadn’t considered myself to be on the verge of. These people had made their decision to squeeze as much pleasure out of life as their circumstances, and the country’s economic construct, would allow. It was fun, more than fulfillment, that drew them here. The Edenic lure of retirement had once been a bit of a mirage: by the time you got to it, you were hardly able to make the most of it. But now earlier retirement (or semi-retirement), better health, increased longevity—at least for some—and the emergence of an infrastructure to accommodate these circumstances have created a stage that may not have existed before. It’s hard to know whether this is something to look forward to or to dread.

We funnelled into the arena, amid that turnstile exuberance I recognized from playoff games and Grateful Dead shows. Hawaiian shirts, group photographs, parrots on heads. We had floor seats. The stage was set with fake boulders and sprouts of seagrass, with big foam models of a crab, a pelican, and an octopus. (The “SpongeBob” scenery reminded me that Buffett had produced a Margaritaville musical on Broadway some years ago—a rare flop for him.) The backdrop was a giant screen, which, as the band took the stage, displayed various shark patterns and cartoons. “Hello, Orlando!” Buffett called out, and kicked into a new song called “Down at the Lah De Dah”:

Down at the Lah De Dah
There’s a perfect margarita in a mason jar
At the end of the world in a sea of dreams
Where the ocean smiles and the seagulls scream
We all know just how lucky we are.

Buffett wore flip-flops, shorts, and a Hawaiian shirt. Tanned and fit, he hopped around and smiled broadly, a paragon of health—attitude, movement, money. He was backed by a dozen musicians, many of them legit hot shit, on drums, percussion, steel drums, pedal steel, two keyboards (featuring Buffett’s longtime bandleader, Mike Utley, and his son Mick Utley), horns, bass, two guitars (including Buffett’s trusty sidekick, the Nashville ace Mac McAnally), and a pair of backup singers in light, flowing multicolored prints. The next song, following the land-shark intro I remembered from the gym, was “Fins.” Thousands of grownups sang along while holding their hands together over their heads and swerving left and right. Few were wearing masks. When in Orlando: I had pocketed mine, too.

I knew more of Buffett’s work than I’d thought. The night went by in a wash of gentle, well-rehearsed and well-worn folk rock, amid video imagery of reefs, coves, beaches, sailboats, cocktails, Jet Skis, cheeseburgers, and resort developments—a kind of subliminal indoctrination into the blurred line between the wild and the tame, the pristine and the industrialized. His patter was humble: “I was a nobody from nowhere and now, thanks to you all, we’re somebodies up here.” “I was just trying to go to Key West to score some weed and find a girlfriend.” “Simply put, if you don’t like Tom Petty, you ain’t shit.” He finished his set with “Margaritaville”—salt, salt, salt. In the row in front of me, a man who looked to be in his sixties was making out with a woman on his left and one on his right. I assumed they were from the Villages. Next to them were two young frat guys who, as the crowd cheered for an encore, attempted, without success, to start a chant of “Let’s go, Brandon.” They could have been from anywhere.

Three more numbers—“A Pirate Looks at Forty,” “Southern Cross,” “Floridays”—and the masses poured out into the streets. The Latitudeners boarded their buses and headed home. I said my farewells and flew back to winter, pants, and high taxes. Five days later, I had Covid, and I couldn’t get the chorus of “Margaritaville” out of my head. ♦