Living the Life of a Long Island Cabana Boy

From hot sun and hurricanes to beach chairs and shady vodka, a look into one of the East Coast’s weirdest seasonal gigs.

A light load.

Each sunny summer morning, five days a week for seven years, my routine was the same. I’d stumble out of bed between 7 and 8 a.m., woken by alarm, parent, or younger brother. I’d shower and throw on my uniform: battered flip-flops, khaki shorts, a pair of dollar-store sunglasses, and a kelly green T-shirt emblazoned with a white arrowpoint and the words “Silver Point” over my heart.

Forty minutes later, my beat-up minivan would roll through the gatehouse and into the parking lot of Silver Point Beach Club in Atlantic Beach, N.Y., with one or more of my brothers and friends inside. Cabana personnel all.

If you think of private Long Island beaches and their cabanas and envision the sultry glamour of The Flamingo Kid, think again. The sun is punishing, the beach chairs are heavy, and the people you meet will alternately drive you up the wall (or down the boardwalk) and remind you of the beauties of human connection.

For one, workers don’t begin at the cabanas, but as “runners.” From ten to five, they sit on a wooden bench and broil, staring into the middle distance as the dusty blacktop fills up with overly large cars packed with noisy kids, bulky groceries, beach furniture, and alcohol.

Ideally, you’d beat one of the other runners to the car, remove its contents, and place them in a decrepit rickshaw cart. Then, usually while a deeply tanned white woman cursed at her kids and spat orders at you not to drop anything, you’d drag the cart a fifth of a mile to a cabana, unload it, and receive, on average, one to three bucks for your trouble.

After a year or so as a runner, depending on how management evaluated your performance, you’d be promoted, likely either to lockers — low effort, despit lots of lugging, but also low reward — or “relief,” a regular substitute for full-time cabana boys. The product of a neurotic family with a supercharged work ethic, I ended up in the latter camp, by far the more coveted position.

Four days a week, I’d regularly substitute for one of two cabana boys (or girls) on their days off — opening cabanas, planting umbrellas and hobnobbing with club members in the hopes that they’d recommend me to management as a replacement once their cabana personnel retired. On the fifth day, I’d work on the maintenance team, where slow days meant shooting the breeze on the porch with our chain-smoking club manager and his cronies.

A quiet day.

Other days, the work would pile up. After a hurricane left the seaside blanketed in rotting seaweed, six of us raked the rancid stuff up for hours and, handful by handful, shoved it into black garbage bags. The designated driver of the club’s all-terrain vehicle — at that time, an Irish exchange student notorious for driving drunk and sleeping with female club members on the sly — refused to hitch us a ride to the dumpsters. We had to drag bag upon bag down more than a mile of boardwalk and through a bird sanctuary located on club property. During nesting season. When we returned to the porch, we had been pecked relentlessly by irate terns and covered in bird droppings. The club manager nearly fell off his chair from laughter.

On one of my off days that same year, I worked overtime at a beachside wedding for a Jewish couple in their 60s — call them Evelyn and Arnold. Each was getting married for the third time; each was ill-tempered and, worried that they had not acquired enough alcohol for the event, convinced that their favorite drink was the best choice for the guests. Evelyn preferred sangria, and Arnold beer and vodka.

“Evelyn,” Arnold sniped after minutes of bickering, “sangria is for women and for fags. Nobody’s gonna drink the damn sangria. We need more vodka.”

At that moment, Evelyn’s son arrived holding an enormous jug of suspiciously unmarked vodka. Evelyn exploded, and I, disgusted, ran for the relative peace of the parking lot.

The cabana boy spends most days repeating the same laborious tasks. Once I’d finally secured my own court of cabanas, I’d spend hours opening doors, putting picnic tables in place, and dragging cart after cart of beach chairs, lounges, coolers, and umbrellas to the shore.

There, I’d plant upwards of 40 umbrellas in the sand per day, accompanied by more than a hundred chairs. All for the sweet influx of untaxed cash tips on Sunday.

Woody Allen movie prop, found.

Yet the sheer quirk of the context offset the downsides and the doldrums of the gig. I’ve worked for a tracksuit-clad member of the Gambino crime family (self-proclaimed), and for a woman who would read nearly a novel a day, sprawled across a lounge chair beneath a Coca Cola umbrella from a New York street cart. I’ve been asked to plant a tree in the sand and, upon my protest that crushed rock can’t nourish a such an organism, heard in response: “But it’s a beech tree!” I’ve seen two fishermen catch a 300-pound stingray from the shore, and watched a blue heron, far from home, settle on a lifeguard stand as the sun set on Labor Day.

After four years of working the same court, my clients became, in a way, family. Unlike other service jobs like waiting tables, cabana personnel tend to serve the same clients regularly for years. That means knowing whose daughter just graduated from which college, what cabana only stocks low-calorie drinks because its occupants own a yoga studio, which members stow THC oil in the cabinet, and who’s prone to sharing their treasures.

Most nights, when older couples and families with small children began to leave, I’d sit with one couple — a widow and a widower, remarried to each other — and the occupants of the cabana next door, an Italian-American family with hippie-era musical leanings and two whip-smart kids.

Someone would throw on Steely Dan or Al Green and sneak beer into a floral-patterned cup, passing it my way as we dug into eggplant parmesan or schnitzel or chicken Marsala. We’d talk weather, books, TV, current affairs. We didn’t all agree on politics, but we discussed them often, and with a gentleness and understanding that seems particularly hard to find these days. It felt, often, like living in another time.

And in a way it was. I’ll never have a farmer’s tan like that again.

Thanks for reading! If you liked this piece, you may also enjoy this piece on The Woman in the Dunes and how it reminded me of my cabana boy days.

Books and toons, moons and Junes. Edits: @publisherswkly, @thedotandline. Words: @esquire, @pacificstand, @polygon, @thrillist, @realsimple, @timeinc, others.