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Margaritaville and the Myth of American Leisure

Margaritaville, as Parrotheads will tell you, is a state of mind. But it’s also — delightfully, sometimes inexplicably — a real place now open in Times Square.

A woman laughs in a teal booth on a rooftop with the sun and skyline in the background.
The 5 o’Clock Somewhere Bar at Margaritaville Resort Times Square.
Jaya Saxena is a Correspondent at, and the series editor of Best American Food and Travel Writing. She explores wide ranging topics like labor, identity, and food culture.

The 5 o’Clock Somewhere Bar does not open until 5 o’ Clock, which puts a crimp in trying to live out the metaphor of its name. The whole point of the phrase is a justification to start drinking early, before the workday is done, because somebody, somewhere is off work. But no, for the 5 o’Clock Somewhere Bar, one of four restaurants and bars at Manhattan’s new Margaritaville Resort Times Square, you must wait until the workday is over. I am furious about this. Sure, the License to Chill Bar opens at 2, but it’s the principle of the thing. Jimmy Buffett would not wait until the boss says you can go home.

The Margaritaville Resort Times Square sounds like an oxymoron. “Resort” conjures pristine beaches with reservable cabanas, room service delivered with an orchid, spas, and restaurants that will just charge your room, so you needn’t worry about even carrying a wallet on the grounds. To me at least, it does not mean a 32-floor hotel in Times Square. Like, I have been to a Times Square hotel bar before, and while I’ve enjoyed myself, it has never been a transformatively relaxing experience.

I’m biased though; being from here makes it hard to view the city through a tourist’s eyes. But while I can picture wanting to visit New York for many things — the museums, the theater, the history, the chance to meet a pigeon who’s eaten a whole slice of pizza — I can’t imagine coming here to engage in leisure. The kind of leisure where you get on a plane and check into a resort just to not leave for a week, to see no other sights besides the novelty tiki drink cups lining the hotel’s bars.

But this is the kind of leisure Margaritaville is built on. Almost all the Margaritaville restaurants and resorts — a vaguely tropics-themed hospitality empire inspired by one of Jimmy Buffett’s most popular songs — exist within massive tourist destinations like Cozumel, Mexico, or Atlantic City, New Jersey. On the surface, Times Square feels like a natural addition. But while other locales can at least offer some seclusion from the world in the form of a beach or an island, Times Square is in the middle of everything. It is hectic, crowded, overpriced, and blatantly capitalistic, a place where no one actually lives and few New Yorkers hang out unless they’re seeing a show or bringing their out-of-town niece to the Disney Store. It has no chill. But maybe the point is it’s not unsalvageable. Amid the stress and the noise, if you delude yourself enough, you can turn off your brain and have fun. So for 24 hours, I tried.

A giant blue flip-flop is encased in glass in a hallway as a man walks past it.
Flip-flop, busted, at the Margaritaville Resort.

Walking into the resort on the lower border of Times Square, at the corner of West 40th Street and Seventh Avenue, I am first greeted by a statue of a gigantic blue flip-flop, with one of the straps busted, and a gigantic discarded pop top just in front of it.

If you are a Jimmy Buffett fan, you probably already get the reference (if not, look up the lyrics to “Margaritaville”). The entire resort is like if Ready Player One was only Jimmy Buffett references. There is a painting of a naked woman made to look like a parrot, asking, “Can you spot the ‘woman to blame’?” There is live-laugh-love-esque wall art of lyrics and sayings as generic as “strummin’ on my six string,” “thank God the tiki bar is open,” and a pillow in my room that read “changes in attitude, changes in latitude.” The surfboards on the wall of the Landshark Bar & Grill ask you to put your “fins up,” and the televisions on the walls play footage of Parrothead (Jimmy Buffett fan) tailgates. Oddly, I did not actually hear a Jimmy Buffett song for many hours.

I wore a tropical-print shirt and sandals to get in the mood, but when the concierge complimented my choice during check-in, I felt like I had worn the band’s shirt to the concert. I dropped my stuff in my room — which was all white and teal faux-clapboard, evoking breezy porches that none of the rooms seemed to have — and headed out for my first meal.

When I was a teenager my mom and I spent a spring break driving around the Florida Keys, and I ate coconut shrimp every single day. This, to me, was luxury, and also what I assume retirement is like. So I figured that should be my order at the Landshark Bar & Grill on the building’s sixth floor. The restaurant opens out onto an actual patio covered in sky-blue lounge chairs and yellow umbrellas, which surround a pool that was torturously not open (they were waiting on a last inspection). Laying in a chaise by the pool with my Pink Cadillac margarita would have really been resort life, but instead I settled for eating my coconut shrimp with coconut ranch (??) at a table next to it. My partner got a lobster roll and some drink that came with a full wedge of pineapple in it. We ate everything, but decided it all tasted lightly of sunscreen.

Still, eating at a table next to the pool was relaxing in its own right; something about having water nearby did distract from the Midtown of it all. I felt the sun and the breeze, and saw a woman with daiquiris embroidered on her lime-green T-shirt. I’m doing it, I thought, I’m relaxing. I made a mental note to return to Landshark once the pool opened and we headed one floor up, to the License to Chill Bar.

Coconut shrimp on a bed of fries on a wood table with yellow chairs in the background.
An artwork with a woman in a taxi saying “Shopping Can Wait, Take Me Back To Margaritaville!”
An outdoor swimming pool with yellow umbrellas and teal loungers.
A hotel room with a bed overlooking the city.

The vaguely tropical theme is woven throughout the resort, from the coconut-fried shrimp to the beachy guest room’s pillows.

Margaritaville does an incredible job of catering to every type of person who might be in Times Square. While Landshark may have been for Parrothead tourists or New York Times employees on an ironic lunch break, License to Chill is more like an outdoor wine bar, with cushioned bucket seats that looked like the baskets I learned to weave in Girl Scouts, and a fireplace that was thankfully not lit in July. Also, for some reason, there was a screen showing a live feed of the traffic at the intersection right outside the hotel, in case you wanted to keep tabs on the WEED WORLD truck parked on Seventh Avenue.

I ordered an $18 drink with “botanicals” and ginger syrup, and my partner got what was basically a $20 gin and tonic. We nestled into our bucket chairs and took out our books, and for two hours, decided to lounge and read while our drinks slowly sweated. To my shock, I could barely hear any traffic, and as I snuggled into the pile of pillows, some emblazoned with a compass to let you pretend this was an exercise in great world adventuring, I did feel distant from home. Then again, I reminded myself, that was probably because this was all going to be on Vox Media’s dime. I’m technically here for “work” and not spending any of my own money. So of course I’m not worried about anything, except how to properly waste away.

The song “Margaritaville,” which forever solidified Jimmy Buffett’s persona as the king of the beach bums, was off his eighth album, and it only took seven years between the release of “Margaritaville” the song (1977) and the opening of Margaritaville the restaurant (1984). The first location was in Alabama, as Buffett couldn’t get the trademark rights in Florida for the name “Margaritaville” because “there are so many using the name around the country,” he told the press at the time. Eventually, he won.

Margaritaville, the one Buffett sang about, is actually an awful place. He allegedly wrote it after ordering a margarita in Austin, Texas, and was also inspired by an influx of tourists to Key West, Florida, where he was living at the time. It’s about a man “wastin’ away” in a touristy beach town, whose only solace from hinted-about heartbreak and foot injuries is tequila. This is not a song about someone who rejects the pressures of workaday life in order to pursue radical pleasure. This is about a man who is depressed and perhaps on the run from the law, for whom shrimp and sea and tattoos provide no peace, and who needs blended beach drinks to “hang on” to whatever semblance of a life he has left. It is not escaping. It’s fleeing. And it’s sort of pathetic.

But fans have instead turned it into a “national anthem for generations of college kids on spring break, burnt-out stockbrokers, and wishful thinkers who long to leave careers behind and let their biggest worry be which beach to sleep on that night,” wrote Dan Daley for Mix. The song has been completely recontextualized so that not even Jimmy Buffett himself can declare this man’s life an unsalvageable mess. Instead of a song about despair, it’s a song about defiance, insisting despite all evidence to the contrary that you are having a good time.

It’s a specific type of fun, though. Jimmy Buffett made his name with “gulf and western music,” a style that combines American country and rock with instruments and tonalities more commonly found in the Caribbean. But while his songs are full of steel drums, lyrically they are mostly about being a white American man dreaming of a Bahamas without Bahamians. It’s an overworked man in a bar, imagining moving to an island paradise, without all the pesky stuff that’s already on the island. There are now more than 60 Margaritaville bars and restaurants across the U.S., Mexico, Canada, and the Caribbean, selling this fantasy of “island” drinks and American foods with coconut or pineapple added to them, sometimes on top of the very places those flavors were taken from. It’s a shame, but not a surprise, how popular a sell that is.

People mingling around a bar and in booths on a rooftop restaurant with the city in the background.
5 o’Clock Somewhere Bar opens at (not before) 5 p.m.

I called another friend to join in the festivities, and he arrived just as I was about to doze off in my bucket seat. By then, it was 5:30, and we were finally allowed to head up to the two-story 5 o’Clock Somewhere Bar, on the hotel’s top floors with views of nearly the whole island. There was barely a smack of Jimmy Buffett there. Inside there were smooth midcentury modern chairs and tasteful patterned wallpaper. A woman with a guitar was singing mellow pop covers. On the outside deck, aqua booths were separated by fabric ferns, and the bar was lined with brushed-brass cocktail shakers. The altitude also seemed to have a filtering effect on the clientele. Except for a group of clearly teenagers, who I assume were served mocktails, trying to live out some joke of an adult night (why does every group of teens trying to go out on the town consist of five girls in cocktail dresses and sparkling chokers, and one gangly boy in jeans who never talks?), the patrons looked like they were all meeting for a 10-year business school reunion. I stared as they ordered Landsharks and drinks named “All Right, All Right, All Right” with straight faces. They knew they could go to any other rooftop bar in Midtown, right? The place is lousy with them! And they all look like this! Was it a joke that they were here or did they all also love Jimmy Buffett? Finally, a man in a Phillies “Margaritaville Night” giveaway shirt sat at the booth next to us, and I felt some sense of normalcy again.

I could see why the business bros wanted to be here, though. Despite all having names like “Jamaica Mistaca,” the drinks at the rooftop bar were of the upscale kind that perhaps warranted the $20 price tag, or at least the aura of wealth. Instead of the juicy, sweet frozen daiquiris of 25 floors down, these were made with things like allspice dram, pineberry, and yuzu puree. Drinking a “W. 40th St & Agave,” a margarita made with Earl Grey agave, and looking out over the Manhattan skyline, I felt... sophisticated? Rich? If not like Shiv Roy, then at least like Cousin Greg? This is my city. This is my time!

At this point, I had not had anything to eat since the coconut shrimp. Neither bar’s kitchen was open yet, which once again reminded me that while it may be 5 o’clock literally here, the spiritual essence of 5 o’clock evaded me. My plan of having a snack of ceviche or wagyu sliders to tide me over was foiled. I switched to wine, but I was still many strong drinks in. I kept referring to being in Manhattan as “being on island time.” I felt far away from all my problems, most likely because I was drunk, but also because my surroundings were so different. I had, in the parlance of the resort, escaped. Finally, it was time to descend to the main event.

The Margaritaville restaurant within the Margaritaville resort takes up two floors. The walls are lined with the same TVs playing the same footage of Parrotheads, the floor-to-ceiling windows give you a great view of the Lot-Less discount store across the street, and in an atrium-like space in the middle, there is a massive Statue of Liberty bust holding a margarita instead of a torch that takes up both stories, big enough that it can be seen from the street. The giant Statue of Liberty rules. It just rules. It’s so cool. I’m drunk and I’m screaming and I am ready to fight the people who get to eat at the lone table inside the giant Statue of Liberty because I want to sit in there so badly.

After the pseudo-sophistication of the upper floors, the Margaritaville restaurant smashes vacation resort vibes with the madness of Times Square tourism. It is LOUD. There are novelty glasses everywhere. My friend Dan and I order various takes on punch, while my spouse gets a “Lime In D’Coconut,” and we ponder how much Jimmy Buffett wishes he had written that song, which is actually good. It comes with an extra can of coconut Red Bull, a flavor I didn’t even know existed.

As we shared our Caribbean chicken egg roll appetizer, I was reminded of a time my spouse chatted up a tourist on his way back to LaGuardia airport while they were both on the bus. The tourist said he loved the city, but complained of the food being too expensive. My spouse said that’s quite possible, but that there was plenty of amazing, affordable food to be found, and asked where he had eaten. The tourist said he and his daughter went to the Times Square Red Lobster. I know these large chain restaurants exist because they are popular, because they are fun or family-friendly or because in a trip probably full of decisions and risks, ordering a burger at a restaurant with name recognition is at least one thing you don’t have to worry about. Here at Margaritaville, I frankly didn’t care what I put in my body, I was just having fun and taking in the fact that on one TV they were playing footage of Parrotheads, and on another was Nancy Pelosi talking about the January 6 riots.

But the mediocrity of my fish tacos almost pulled me out of it. They were grilled and dry and slightly mealy, served with plain rice and black beans that tasted like they had just been dumped out of the can. I was suddenly too aware that I was not actually on vacation and that all the pressures I desperately needed a break from were going to need my attention tomorrow, and that some might be filling up my text messages at that very moment. There were CSA vegetables in the fridge that needed to be cooked before they turned, and invoices to send, and family to check in on, and a job that I was technically at that I hadn’t gone on an actual vacation from in a year and a half because of a global pandemic, because oh God I need my job, I need health insurance, everything hinges on this. And I was too aware that there were other restaurants in this city, other things I could be doing that would make me happier, but instead I was here. I was working. I was not escaping. There was no escape.

Then, suddenly, the lights went out. From behind me, music started blaring even louder than it already had been. Something was happening with the giant Statue of Liberty. Dan and I jumped out of our seats and ran to see a light show projecting onto her majestic margarita, choreographed in time to the music. There were neon dolphins, erupting coral reefs, flames giving way to ice cubes fading into a shimmering mirror ball. It was overwhelming like Times Square is overwhelming, and for the first time I understood how this level of light and noise could be awe-inspiring rather than just annoying. It forced all other concerns and worries out of my head and replaced them with the phrase DISCO MARGARITA. It was aggressive, it sent me to the edge of my joy and had me teetering on panic, but I couldn’t think of anything else — the taco-induced, work-is-killing-me crisis of moments before was gone. No thoughts, just Buffett. I became aware that, for the first time that day, “Margaritaville” was playing.

Tourists dine on wood tables in a tropical dining room.
A blue drink sits on a table with three fish tacos with rice and beans.
The exterior of the Margaritaville Resort Times Square.
A statue of liberty holds a giant margarita that is projecting flames.

The two-story Lady Liberty and her psychedelic margarita is the centerpiece of the resort’s main event: the Margaritaville Restaurant.

The 5 o’Clock Somewhere bar wouldn’t exist if work didn’t end at 5 o’Clock. The U.N. Universal Declaration of Human Rights, adopted in 1948, states in Article 24 that “everyone has the right to rest and leisure, including reasonable limitation of working hours and periodic holidays with pay.” This article came after, and seems likely to have been influenced by, labor movements around the world at the turn of the 20th century, as activists campaigned and died for things like a weekend, or the eight hour workday. The concept of leisure, what economist Thorstein Veblen defined as the “non-productive consumption of time,” for anyone but the richest classes, was still new in the 20th century. But by 1948 more people had time for it.

In The Theory of the Leisure Class, Veblen outlines the concept of conspicuous leisure — essentially being nonproductive in order to brag about it, rather than for your own rest and self-betterment. At the time he wrote it, he said it was a behavior of the idle rich, who would rather risk whittling away their fortune by devoting their days to obscure hobbies than work a factory floor. But as the middle class grew and labor protections were enshrined, especially in America, leisure time began to be more available, and began to resemble the activities that previously belonged to only the wealthiest. In 1950, the French Club Med pioneered the all-inclusive resort, which seemingly overnight existed everywhere. You could drive to Florida or California, or fly to Hawaii. You could do nothing, but do it somewhere exotic, and bring a souvenir back to show everyone. Tans, bikinis, and a drink in hand. A beach at the end of the world.

People of all classes can now engage in conspicuous leisure, or at least emulate it. Not to be all “everyone be on their phones,” but leisure increasingly exists to be simultaneously documented and publicly acknowledged. A resort like Margaritaville is foremost designed to be looked at: the novelty of sitting by a pool in Midtown, the overwhelming Statue of Liberty light show, the view from the rooftop bar. However, conspicuous leisure has taken on a different flavor as it has spread. The rich who spent their days breeding dogs did not have a job to return to at the end of the week. The rest of us do. So when we engage in conspicuous leisure, there is a tinge of anxiety. Staying at Margaritaville may not result in anyone’s rest or self-betterment, but we need to convince ourselves it does. And we do that by trying to convince others it has.

A woman pours a drink behind a bar where one man sits on his phone.
The tiki-ish Margaritaville bar.

In America leisure only exists in relation to work, and we are a culture that fetishizes work. Even leisure, that nonproductive time, is spoken of through its value to production, how we all need time off so we can be better workers when we return. And our leisure time is being eroded. “In a number of developed countries, steady jobs – with benefits, holiday pay, a measure of security and possible union representation – are increasingly giving way to contracts,” warns the U.N.’s Office of the High Commissioner for Human Rights. Workers in the U.S. take relatively few vacation days compared to workers in other countries, maybe because we aren’t afforded any paid time off on a federal level, and often work far longer than eight-hour days. Dolly Parton bastardized her own ode to the working woman by releasing “5 to 9” as part of a Super Bowl ad, an uncritical appreciation of working more in one’s free time. People aren’t even guaranteed paid time off to get the COVID-19 vaccine.

That culture of hustle and greed disguised as effortless relaxation created Jimmy Buffett and Margaritaville. Many of his songs, and now his resorts and restaurants, and the entire aura he projects, are about escape from your life, which assumes your life is something you want to escape. If the inspiration for Margaritaville is a song about a man who has left it all behind to do nothing, the resort may as well be a theme park for conspicuous leisure — you too can leave it all behind, and then come back and brag about how you left it all behind to assure yourself you indeed did that. Leisure becomes an exercise in labor. The “eight hours for what we will” the Wobblies fought for is increasingly slipping away. You have this rare opportunity for nonproductive time, something to be scrimped and saved for, so you must chill out. You cannot waste this.

In short, the whole ethos behind the resort is acknowledging that work sucks and no one wants to do it, but that ethos can only thrive in relation to work. If work didn’t suck, no one would be there. Though the executives behind the Big Flip-Flop may not have intended it, there is a desperation in the song “Margaritaville” that permeates the Times Square resort. Entering the building was like signing a contract, that everyone here is agreeing to buy into the facade so as not to kill the vibe. Everyone here needs this, on some level, and while I’m also aware of the organized fun of it all, I also need it.

As I returned to the 5 o’Clock Somewhere bar for a final drink before collapsing in my room, I thought of what Margaritaville might look like if we acknowledged we had enough resources to go around, that no one has to work as hard as they do for as little as they get. What would a vacation, a nice meal, or a rooftop cocktail look like if it didn’t have to carry so much weight? I don’t think it would involve a two-story light-up Statue of Liberty. For a second, that makes me sad.

The next morning I realized my mission to not leave the resort would be nearly impossible when it came to breakfast. The room came equipped with two bottles of water and a Keurig machine with four coffee pods (one of which was, surprise surprise, coconut coffee). However, there was no cream or sugar, and the mini fridge was empty. I scrounged the drawers for a room service menu and found there was none, and when I attempted to call the front desk, there was no dial tone. The restaurants didn’t open until 11.

Still, there was the Joe Merchant’s Coffee & Provisions stall in the lobby, and I thought there might be at least something to eat there. I took a shower with St. Somewhere Spa-branded body wash that smelled mostly of teenage-boy cologne, and went downstairs, hoping to find a Calypso Breakfast Sandwich or Parrothead Parfait or whatever weird beach-branded meal they offered. Instead, I found a mediocre bodega, with plastic-wrapped bagels and tuna sandwiches and granola bars. I could find this, and better, outside. I wanted to go back outside.

My partner and I packed up and left. We got bacon, egg, and cheese sandwiches and iced coffee on the way home, and since we had already budgeted having that afternoon off, we enjoyed them on our real-life balcony in the sun. I took a midday nap on the couch, content in the knowledge that there was nowhere I had to be and nothing I had to do at that moment. It could be like this all the time. It’s always 5 o’clock somewhere.

The New York City skyline with the sun setting behind it.
Sunset (and sunrise) views over the city from the Margaritaville Resort Times Square.

Clay Williams is a Brooklyn-based photographer.

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