A Few Nights in Two Florida Keys Resorts, in Search of the All-American Beach Vacation

Welcome to Beach Week, our annual celebration of the best place on Earth. This story is part of One Night In, a series about staying in the most unparalleled places available to rest your head.

In my mind, "beach vacation" is redundant—and fans of novelty wall plaques inscribed with phrases like "life’s a beach" would probably agree. According to Smithsonian, it was only in the 18th century that the beach went from being a place that was feared to one that was sought after, a site where wellness could be gained. (We even have the stalwart deck chair as a result of related efforts toward health and leisure.) "Travel became affordable and easy," writer and historian Daniela Blei explains in the Smithsonian article. "Middle-class families took to the shore in ever-increasing numbers. In sailors’ jargon, ‘on the beach’ once connoted poverty and helplessness; being stranded or left behind. Now it conveyed health and pleasure. The term ‘vacation,’ once used to describe an involuntary absence from work, was now a desired interlude."

In American culture, the beach is prized more than most places, perhaps due to the fact that a wide swath of our country is located nowhere near one. Resorts as we now understand them grew in the 1900s, and by the ’70s, were a relative norm of travel. Kid-friendly (and all-inclusive) hotels have become a category unto themselves, a place parents can relax as much as one can when one has a child, while not having to ship their progeny off somewhere else to get the relaxing done. In the U.S., there is no place that has more beachfront hotels than Florida, a state that also owns the distinction of having the furthest point south: Key West. And while Florida has recently suggested it would like fewer people to come enjoy what it has to offer, spring break in all its forms—be it MTV or geriatric—lives on a hundred years after its original conception.

None of this culture has ever been a part of my lived experience; growing up in New York, with our closest family in Los Angeles, meant that my main vacation every summer was to, yes, Malibu: one of the most coveted beaches in the world, idyllic in a very different way. (I can’t leave out the time we spent in a family friend’s shack on Cape Cod either.) But I always casually wondered what exactly I was missing. So in March, more than two decades after my mother and sister and I rented a small bungalow apartment in Key Largo and I ate lobster tail for the first time, marking a lifelong obsession with the crustacean, I made it my mission to compare two (from what I could tell) typical Florida Keys beach resorts, each at a different spot along the drive. Adding to the themes I was going to explore on this trip, I coerced two of my best friends into aligning our schedules and going on vacation together. (Girls trip!) What is so appealing about the beach resort lifestyle? Well, there’s no time like peak spring break to find out.

Thursday

10 a.m.: We flew into Miami the night before, got a quick dunk in the pool, and ate dinner, before heading out early to the Everglades, a part of Florida I’d never been to. After an airboat tour and a walk around a small section of this vast wetlands, during which I got perhaps too close to some alligators for comfort, we drove down to the Islander Resort in Islamorada, Florida. The full Keys drive is, without traffic, about three and a half hours, and this town, one of the larger in the Keys, sits toward the top. It still very much maintains the beach town vibes you can experience almost anywhere: bathing suit shops, snorkel spots, and leisurely bikers alongside the two-lane highway that at points basically takes up the full span of land, bright turquoise ocean on either side. The resort is chillness incarnate; though it has over 100 bungalows and suites, and over two dozen villas, the low-slung buildings surrounded by palm trees feel modest, beckoning you to the beach and pools.

4 p.m.: We check in to our Ocean View Queen, which, had I not reached out about a comped visit, runs several hundred dollars a night dependent on the season, drop our stuff off and head straight to the ocean, walking past the sports area that features a putting course, beach volleyball, and bocce ball, among other activities. Never having experienced the all-inclusive lifestyle, I’m marveling at all there is to do, should I desire to do anything but lay down. After a plunge into the water—the Keys aren’t known for their beaches, since they are largely reef, and the Islander is one of the rare hotels to have beach access—we head over to the two pools, which are surrounded by relaxing families. All the men I see are all wearing variations of the same surf-branded clothing, wraparound sunglasses, and slight to aggressive sunburns. After a highly serviceable piña colada from the Tides Beachside Bar, we park ourselves in the water at the pool that seems slightly more adult-friendly, and enjoy the fruits of our labor (driving a few hours successfully).

6 p.m.: After a shower with Malin + Goetz products—including body lotion in a tube that I loved—and a brief lie down in my hotel-provided robe and we’re ready to hit the town, which means walking (or scampering swiftly) across the highway to Lorelei (you can’t miss the gigantic mermaid sign), which I’ve read is the spot for sunset viewing. It’s absolutely packed in a good way, and I avail myself of their "World Famous Key Lime Colada," which tastes exactly like key lime pie in a cup, complete with graham cracker on the rim. There are many more sunburned people here, and children racing around the tables in the sand past the bar, and we enjoy said sunset while waiting for ours. Once seated, I order the Florida lobster (smaller than our Maine friends), and we listen to the jam band of the night, who has allegedly been performing here for decades, every night likely identical to the one before. The night takes on a chill and a set of teens take turns taking glamour shots of one another against the darkening sky and water. As we exit, ready to cuddle up in bed at a geriatric hour, a group of college-age women is just getting seated and starting their night. Here, all ages find their place.