Margaritaville and the Illusion of American Leisure

The 5 o’Clock Somewhere Bar doesn’t open until exactly 5 PM, which complicates the very spirit of its name. The idea behind the phrase is to allow early drinking before the workday wraps up, because somewhere, someone is off the clock. Yet, at this bar in Manhattan’s Margaritaville Resort Times Square, you have to wait until the official end of the workday. This frustrates me. Sure, the License to Chill Bar kicks off at 2, but it’s a matter of principle. Jimmy Buffett wouldn’t stand by waiting for the boss to release him.

The Margaritaville Resort Times Square feels like a contradiction in terms. “Resort” brings to mind idyllic beaches, reservable cabanas, seamless room service, and spas where you can forget your wallet. To me, it doesn’t mean a towering 32-floor hotel smack in Times Square. I’ve enjoyed Times Square hotel bars before, but they’ve never been places of true relaxation.

I admit I’m biased; being a local makes it hard to see the city through a visitor’s lens. While I can imagine traveling to New York for countless attractions—the museums, the history, or even a pigeon that’s devoured a full slice of pizza—I can’t picture coming here solely for relaxation. The type of leisure where you fly to a resort just to stay put for a week, missing all the sights apart from the novelty tiki mugs at the hotel bars.

Yet this is the essence of leisure that Margaritaville embodies. Most Margaritaville establishments—a hospitality chain inspired by one of Jimmy Buffett’s hit songs—thrive in popular tourist spots like Cozumel or Atlantic City. At first glance, Times Square seems like a fitting addition. But unlike those locales that can offer a bit of escape, Times Square is a bustling hub, chaotic, expensive, and overtly commercialized, a place where few residents hang out unless attending a show or bringing tourists to the Disney Store. There’s little tranquility here. However, perhaps it’s not beyond redemption. Amid the chaos and clamor, if you convince yourself hard enough, you can turn off your thoughts and enjoy. So for a full day, I gave it a shot.

Upon entering the resort at the edge of Times Square, right at the intersection of West 40th Street and Seventh Avenue, I’m greeted by a towering statue of a blue flip-flop, its strap broken, with a giant pop top resting just in front of it.

If you’re a fan of Jimmy Buffett, you likely recognize the allusion (if not, check out the lyrics to “Margaritaville”). The entire resort feels like a version of Ready Player One dedicated solely to Buffett references. There’s a painting of a nude woman transformed into a parrot, playfully asking, “Can you find the ‘woman to blame’?” The walls are adorned with live-laugh-love style art featuring generic lyrics like “strummin’ on my six string” and “thank goodness the tiki bar is open,” alongside a pillow in my room stating, “changes in attitude, changes in latitude.” The surfboards in the Landshark Bar & Grill urge you to raise your “fins up,” and the TVs show footage of Parrothead tailgates. Strangely, I didn’t actually hear a Jimmy Buffett song for several hours.

I donned a tropical-print shirt and sandals to set the mood, but when the concierge praised my outfit during check-in, it felt like showing up to a concert in the band’s shirt. After dropping my belongings in my room—decorated in all white and teal faux-clapboard, reminiscent of breezy porches that none of the rooms seemed to feature—I set out for my first meal.

As a teenager, my mom and I spent a spring break cruising through the Florida Keys, indulging in coconut shrimp every day. To me, this was pure luxury and what I imagine retirement to be like. So, naturally, I chose that as my order at the Landshark Bar & Grill on the sixth floor. The restaurant features an actual patio adorned with sky-blue lounge chairs and yellow umbrellas, surrounding a pool that was agonizingly closed, pending a final inspection. Enjoying a Pink Cadillac margarita while lounging by the pool would have been ideal resort living, but instead, I settled for my coconut shrimp with a peculiar coconut ranch at a table nearby. My partner ordered a lobster roll and a drink topped with a full wedge of pineapple. We finished everything, but everything seemed to carry a hint of sunscreen flavor.

Nonetheless, dining beside the pool was its own form of relaxation; having water nearby provided a nice distraction from the hustle of Midtown. I felt the sun’s warmth and a gentle breeze, and I spotted a woman wearing a lime-green T-shirt adorned with daiquiris. I’m doing it, I thought, I’m really relaxing. I made a mental note to return to Landshark once the pool opened and we moved one floor up to the License to Chill Bar.

The resort's subtly tropical theme is evident everywhere, from the coconut-fried shrimp to the beach-inspired pillows in the guest rooms.

Margaritaville excels at appealing to all kinds of visitors in Times Square. While Landshark caters to Parrothead tourists or New York Times staff enjoying an ironic lunch, License to Chill resembles an outdoor wine bar, complete with cushioned bucket seats reminiscent of Girl Scout weaving projects and a fireplace that thankfully wasn’t lit in July. Curiously, there was also a screen displaying live traffic feeds from the intersection outside the hotel, perfect for tracking the WEED WORLD truck parked on Seventh Avenue.

I ordered an $18 drink infused with botanicals and ginger syrup, while my partner opted for a $20 gin and tonic. We settled into our bucket chairs and pulled out our books, deciding to relax and read for two hours as our drinks gradually sweated. To my surprise, I barely heard any traffic, and as I nestled into the pile of pillows, some adorned with a compass for that adventurous touch, I did feel somewhat removed from reality. Yet, I reminded myself that this was all on Vox Media’s budget, as I was technically here for ‘work’ and not spending my own money. Naturally, I wasn’t worried about a thing, except how to fully embrace the concept of wasting away.

The song “Margaritaville,” which firmly established Jimmy Buffett as the quintessential beach bum, was part of his eighth album. It took seven years from the release of the song “Margaritaville” in 1977 to the opening of the first Margaritaville restaurant in 1984. The inaugural location was in Alabama, as Buffett faced challenges obtaining trademark rights for “Margaritaville” in Florida due to the name’s widespread use across the country, as he mentioned to the press. Eventually, he prevailed.

The Margaritaville that Buffett sings about is, in reality, quite dismal. He reportedly penned the song after ordering a margarita in Austin, Texas, inspired by the influx of tourists in Key West, Florida, where he lived at the time. It narrates the story of a man ‘wastin’ away’ in a touristy beach town, whose only escape from the hinted heartbreak and foot injuries is tequila. This isn’t a tale of someone who liberates themselves from the mundane grind to embrace wild joy. It depicts a man in despair, possibly fleeing from the law, where shrimp, the sea, and tattoos bring him no comfort, and he relies on blended beach drinks to cling to whatever remnants of life he has left. It’s not an escape; it’s a retreat, and it’s rather pitiable.

However, fans have transformed it into a ‘national anthem for generations of college students on spring break, jaded stockbrokers, and dreamers wishing to abandon their careers for a life of leisure,’ as Dan Daley wrote for Mix. The song has undergone a complete recontextualization, to the point where even Jimmy Buffett cannot label this man’s existence as hopeless. What was once a song of despair has become a declaration of defiance, claiming that, despite all evidence, you are having a good time.

This fun, however, is quite particular. Jimmy Buffett carved his niche with ‘gulf and western music,’ blending American country and rock with Caribbean instruments and melodies. While his songs are rich with steel drum sounds, their lyrics often center on the white American man fantasizing about a Bahamian paradise without the actual Bahamians. It depicts an overworked individual in a bar, dreaming of relocating to an idyllic island, blissfully ignoring the complexities of life there. Today, over 60 Margaritaville bars and restaurants exist across the U.S., Mexico, Canada, and the Caribbean, peddling this fantasy of ‘island’ drinks and American fare, often embellished with coconut or pineapple, sometimes on top of the very places these flavors originate from. It’s unfortunate, yet unsurprising, how alluring this fantasy is.

I called up another friend to join the celebration, and he arrived just as I was about to drift off in my bucket chair. By then, it was 5:30, and we were finally allowed to ascend to the two-story 5 o’Clock Somewhere Bar, perched atop the hotel with sweeping views of nearly the entire island. The vibe there was barely reminiscent of Jimmy Buffett. Inside, sleek midcentury modern chairs complemented tasteful patterned wallpaper, while a woman strummed a guitar, performing soothing pop covers. Outside on the deck, aqua booths were divided by fabric ferns, and the bar gleamed with brushed-brass cocktail shakers. The altitude seemed to refine the crowd as well; apart from a group of clearly underage teens, likely sipping mocktails in a misguided attempt at adulthood (why is it always five girls in cocktail dresses and a quiet guy in jeans?), most patrons resembled attendees of a 10-year business school reunion. I watched as they ordered Landsharks and drinks named “All Right, All Right, All Right,” maintaining serious expressions. Didn’t they realize they could go to any other rooftop bar in Midtown, which were abundant? And they all looked the same! Was it a joke, or did they genuinely enjoy Jimmy Buffett? Then, a man in a Phillies “Margaritaville Night” shirt sat next to us, restoring a sense of normalcy.

I understood why the business types flocked here. Despite having whimsical names like “Jamaica Mistaca,” the rooftop drinks were upscale enough to justify their $20 price tags or at least exude an aura of wealth. Unlike the sugary, frozen daiquiris from 25 floors below, these cocktails boasted ingredients like allspice dram, pineberry, and yuzu puree. Sipping on a “W. 40th St & Agave,” a margarita infused with Earl Grey agave while gazing at the Manhattan skyline, I felt... sophisticated? Wealthy? If not quite like Shiv Roy, at least a bit like Cousin Greg? This is my city. This is my moment!

By this point, I hadn’t eaten anything since the coconut shrimp. Neither bar’s kitchen was open yet, reminding me that although it was literally 5 o’clock here, the true essence of 5 o’clock eluded me. My plan to snack on ceviche or wagyu sliders was dashed. I switched to wine, but I was already several strong drinks in. I kept referring to being in Manhattan as “island time.” I felt distanced from my problems, likely due to being tipsy, but also because of the strikingly different atmosphere. I had, in resort terms, escaped. At last, it was time to head down to the main event.

The Margaritaville restaurant within the Margaritaville resort occupies two floors. Its walls are adorned with numerous TVs playing endless footage of Parrotheads, while floor-to-ceiling windows showcase a great view of the Lot-Less discount store across the street. In the central atrium, a massive bust of the Statue of Liberty holds a margarita instead of a torch, towering over both stories, visible from the street. The giant Statue of Liberty is magnificent. It’s just fantastic. I’m drunk, I’m shouting, and I want to fight for a seat at the lone table inside the giant Statue of Liberty because I crave that experience so much.

Following the faux-sophistication of the upper levels, the Margaritaville restaurant immerses you in the chaotic energy of Times Square tourism. It is absolutely LOUD. Novelty glasses are everywhere. My friend Dan and I order various punch concoctions, while my spouse opts for a “Lime In D’Coconut.” We ponder how much Jimmy Buffett must wish he had penned that actual good song. It even comes with an extra can of coconut Red Bull, a flavor I had never known existed.

As we enjoyed our Caribbean chicken egg roll appetizer, I recalled a moment when my spouse struck up a conversation with a tourist on the bus back to LaGuardia. The tourist expressed his love for the city but lamented about the high food prices. My spouse replied that while that might be true, there were plenty of amazing, affordable eats around. When asked where he had dined, the tourist mentioned he and his daughter had gone to the Times Square Red Lobster. I understood why these large chain restaurants thrived; they offer familiarity and safety in a trip often filled with uncertainty. At Margaritaville, I honestly didn’t care about what I was eating; I was just enjoying myself, captivated by one TV showing Parrothead footage and another featuring Nancy Pelosi discussing the January 6 riots.

However, the mediocrity of my fish tacos nearly brought me back to reality. They were grilled yet dry, slightly grainy, served alongside plain rice and black beans that tasted straight from the can. Suddenly, I was starkly aware that I wasn't truly on vacation and that the mounting pressures I desperately sought to escape would demand my attention tomorrow. I had CSA vegetables in the fridge needing to be cooked, invoices to send, family to check in on, and a job that I hadn’t properly left for over a year and a half due to the pandemic. Oh God, I needed that job; I needed health insurance—everything depended on it. I realized there were other restaurants in the city, other activities that could bring me joy, but here I was, tied to work. There was no escaping.

Then, without warning, the lights went out. Music blared even louder, and something was happening with the giant Statue of Liberty. Dan and I leaped from our seats, rushing to witness a light show dancing across her giant margarita, synchronized to the music. Neon dolphins, erupting coral reefs, flames melting into ice cubes, and a shimmering mirror ball filled the space. It was as overwhelming as Times Square itself, and for the first time, I grasped how this sensory overload could be awe-inspiring rather than just annoying. It pushed all my worries aside and replaced them with the thought DISCO MARGARITA. It was intense, teetering between joy and panic, but all else faded away—the taco-induced work stress vanished. No thoughts, just Buffett. I suddenly noticed that “Margaritaville” was playing for the first time that day.

The two-story Lady Liberty, along with her vibrant margarita, serves as the focal point of the resort’s main attraction: the Margaritaville Restaurant.

The 5 o’Clock Somewhere bar wouldn’t exist without the traditional end of the workday at 5 p.m. The U.N. Universal Declaration of Human Rights, adopted in 1948, asserts in Article 24 that 'everyone has the right to rest and leisure, including reasonable limitations on working hours and periodic holidays with pay.' This article followed the labor movements of the early 20th century, when activists fought and even sacrificed their lives for rights like weekends and the eight-hour workday. The idea of leisure, defined by economist Thorstein Veblen as the “non-productive consumption of time,” was still a novel concept for anyone outside the wealthiest classes at that time. By 1948, however, more people found themselves with leisure time.

In The Theory of the Leisure Class, Veblen discusses the notion of conspicuous leisure—engaging in nonproductive activities to boast about it, rather than for personal rest or self-improvement. He observed this behavior among the idle rich, who would rather risk depleting their wealth on obscure hobbies than toil on a factory floor. Yet, as the middle class expanded and labor rights became established, particularly in America, leisure time became more accessible and started to mirror activities once exclusive to the elite. The all-inclusive resort concept was pioneered by Club Med in 1950, appearing suddenly in various locations. You could drive to Florida or California or fly to Hawaii, doing nothing in exotic locales and bringing back souvenirs to flaunt. Think tans, bikinis, and cocktails in hand—a beach paradise at the edge of the world.

People from all walks of life can now partake in conspicuous leisure or at least mimic it. Not to sound overly critical about phone usage, but leisure increasingly exists to be captured and shared publicly. A venue like Margaritaville is primarily designed for visual appeal: the novelty of lounging by a pool in Midtown, the dazzling light show featuring the Statue of Liberty, and the stunning views from the rooftop bar. However, the nature of conspicuous leisure has evolved as it has become more widespread. The wealthy who spent their days breeding dogs didn't have a job to return to at week's end. Most of us do. Thus, when we engage in conspicuous leisure, there's often an underlying anxiety. While staying at Margaritaville may not truly lead to rest or self-improvement, we feel compelled to convince ourselves that it does, often by seeking validation from others.

In America, leisure exists only in relation to work, and we are a culture that idolizes hard work. Even leisure time, which is supposed to be nonproductive, is often discussed in terms of its benefits for productivity, as we’re told we need time off to return as better employees. Our leisure time is also diminishing. According to the U.N.’s Office of the High Commissioner for Human Rights, “steady jobs – with benefits, holiday pay, a measure of security and possible union representation – are increasingly being replaced by contracts” in many developed nations. American workers take significantly fewer vacation days compared to their counterparts in other countries, perhaps due to the lack of federal paid time off, and often endure longer workdays. Dolly Parton ironically twisted her own anthem for working women with “5 to 9,” featured in a Super Bowl ad, glorifying the idea of working during one’s free time. Even getting paid time off to receive a COVID-19 vaccine isn’t guaranteed.

The hustle culture and greed masquerading as effortless relaxation gave birth to Jimmy Buffett and Margaritaville. Many of his songs, along with his resorts, restaurants, and the entire persona he embodies, revolve around escaping from life, presuming that one’s life is something to flee from. If Margaritaville was inspired by a song about a man leaving everything behind to do nothing, then the resort serves as a theme park for conspicuous leisure — inviting you to abandon it all and then return to boast about having done so, reassuring yourself that you indeed escaped. Leisure becomes another form of labor. The “eight hours for what we will” that the Wobblies championed is increasingly fading away. When you finally get this rare chance for nonproductive time, something you have to save up for, you must take it easy. You cannot let it go to waste.

In essence, the entire concept of the resort revolves around the shared understanding that work is undesirable and no one truly wants to engage in it, yet this mindset can only flourish in the context of work itself. If work were enjoyable, no one would seek refuge here. Although the creators of the Big Flip-Flop may not have intended it, there’s a sense of desperation in the song “Margaritaville” that hangs over the Times Square resort. Walking through the entrance felt like signing a pact, with everyone agreeing to embrace the illusion to maintain the atmosphere. On some level, everyone here needs this escape, and while I recognize the orchestrated fun of it all, I find I need it too.

As I made my way back to the 5 o’Clock Somewhere bar for one last drink before retreating to my room, I pondered how Margaritaville might look if we acknowledged that resources are abundant enough for everyone, allowing us to work less for more. What if a vacation, a delicious meal, or a rooftop cocktail didn’t have to carry such heavy expectations? I doubt it would feature a towering, illuminated Statue of Liberty. That thought brings a fleeting sense of sadness.

The following morning, I realized that my goal of not leaving the resort would be nearly impossible when it came to breakfast. The room had two water bottles and a Keurig machine with four coffee pods (one being, of course, coconut coffee). Yet, there was no cream or sugar, and the mini fridge was bare. I rummaged through the drawers for a room service menu but found none. When I tried to call the front desk, there was no dial tone. The restaurants didn’t open until 11.

Nonetheless, I spotted the Joe Merchant’s Coffee & Provisions stall in the lobby, and hoped to find at least something edible. After showering with St. Somewhere Spa body wash that smelled reminiscent of teenage cologne, I ventured downstairs, eager for a Calypso Breakfast Sandwich or a Parrothead Parfait, or any quirky beach-themed meal they might offer. Instead, I stumbled upon a lackluster bodega, offering plastic-wrapped bagels, tuna sandwiches, and granola bars. I could find much better options outside. I yearned to escape back outside.

My partner and I packed up and departed. On our way home, we grabbed bacon, egg, and cheese sandwiches along with iced coffee, and since we had already planned for that afternoon off, we relished them on our real-life balcony under the sun. I indulged in a midday nap on the couch, feeling content in the knowledge that there was nowhere I had to go and nothing demanding my attention at that moment. Life could be like this all the time. It’s always 5 o’clock somewhere.

Clay Williams is a photographer based in Brooklyn.