By Johnson 
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.
A hotel with multiple pools is a must when leaning into the resort lifestyle.
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).
Open-air dining options are also important.
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.
The rooms at Islander Resort are decked out in muted tones and natural materials.
Friday
9 a.m.: The day is a windy one, so we scrap our vague plan of going paddleboarding or out on the water in some way and plan to just chill for a while. First, there’s yoga, which is held in the ballroom because it is literally too windy outside to do it while enjoying the sea breeze; I watch a nine year old do perhaps her first class ever and am very impressed.
Our room and the rest of the hotel—newly renovated—lean into beachy interior design in a highly familiar way. This is no midcentury Floridian design; it’s all neutrals and blues. Think: raffia, a live-edge desk, leather details on the queen beds, and throw pillows. It opens up onto a little outside table area and lounge chairs, a view of tall palm trees, and the coveted and necessary ocean view beyond. There is, of course, a ceiling fan and plantation shutters. If there’s a notable difference in this space over any other like it, it’s the cleanliness of everything—we’ve all been to a beach spot where sand remains on literally every surface, no matter how many times it’s been cleaned—and the clarity that everything here has been chosen with care. Nothing about it screams design; moreso, it’s muted, the backdrop to where you want to be most (outside).
1 p.m.: After an extremely good fish sandwich for yes, breakfast, we situate ourselves for reading at the upper pool for a few hours. Once properly bored, we borrow bikes from the activity center, and bike five minutes down the road to Florida Keys Brewing. I’m not really a beer person, but it seems like an occasion to order a flight and try their wares, along with some tacos and guacamole from the food truck. We laugh at a lengthy sign warning spring breakers to keep it chill and “keep watch over your children” because “last week got a bit out of control.” Not usually the visual you imagine from spring break.
6 p.m.: After biking back, we try out the lower pool, which is curved and has a beach entrance, and listen to this evening’s musical performance: a fantastic steel drums player. Then we get ready and head to dinner at Lazy Days, where I get my second lobster, which is even better than the first, and we share the largest jumbo shrimp cocktail I’ve ever seen.
The property has any kind of seating you could desire for oceanfront relaxing.
Saturday
9 a.m.: The next day is our one bad weather day, so we decide to just check out and head down to Key West, foregoing our plan to yet again snorkel. Regardless of the weather, the drive down, yes, Jimmy Buffett Memorial Highway is beautiful, and I’m as wowed by it now as I was as a kid seeing it for the first time, especially given that that time, we hadn’t made it past Key Largo. We marvel at the fact that there was once a train that took you down this narrow spit of land, its remains viewable as you whiz by.
12 p.m.: Our next stop is the Parrot Key Hotel and Villas. The vibe here is a bit harried; all the guests are at the concierge losing it over the rain. (He doesn’t seem to know what to do when it rains either.) Since we’re so early, our room isn’t ready, so we decide to leave our stuff and get a car to lunch. So much is outdoors in this town that it’s hard to tell where there will be covered seating, but I love a seafood market so we head to Eaton Street Seafood Market to try our best. Stone crab chowder is a must for a rainy day, as is our second fish dip of the trip (they’re all good). Once we’re done, having neglected to ask the hotel for umbrellas, we grab another car and head to the Ernest Hemingway Home and Museum, as it seems like as good a day as any to see it. Though so much of the tour is of the grounds full of riotous tropical plants that surround the famed author’s home where he resided in the 1930s, we still have a fun time during the walk-through, taking in the strong smell of his famous cats.
3 p.m.: I get a call that our rooms are ready, so we head back. We’ve been set up with a waterfront three-bedroom suite, which usually runs at several hundred dollars a night (they also comped my visit). We look at our map—a reminder we’re in Florida: the Gulf of Mexico has been renamed on it—and weave our way past the hotel restaurant/bar. All four pools (one of which is specifically adults-only) are surrounded by vegetation and hidden speakers blasting pop music, making them feel like they’re in the jungle, albeit a jungle-slash-club. The rooms are all housed in two- or three-story stilted town houses, and ours make up half of one full building. They’re designed so they can be used as one, for a family, or two, with one bedroom on the ground floor and the others connected upstairs, including a sitting room with a television and bar. I take the first floor so I can step off the deck onto the sand, which has more chairs and hammocks overlooking the water. The vibe is strikingly similar to where my in-laws have a place in the mid-Atlantic, another bastion of beach culture; the rooms are yet again muted in tones with blues as the pop of color, with tons of space between furniture. I’m beginning to realize that the beach aesthetic, and overall vibe, is: let’s remind you of the outside, you want to be outside, nothing can touch outside. The kitsch you might associate with any rental house in this kind of town is nowhere to be seen here.
Porches on some of the rooms at Parrot Key Hotel and Villas lead off to sand, hammocks, and a view of the water.
6 p.m.: The rain finally lets up and we head downtown again; I assume that, given its size, there were limited options in terms of positioning the hotel near the main drag of Key West, which is quite small and very kitschy. After wandering around a bit, our obvious stop is the famous (or infamous?) Sloppy Joe’s Bar, where the Bret Michaels-looking performer gives way to a fundraiser for…cats? We order yet another house specialty, the “Award Winning Sloppy Rita” (Cazadores Reposado Tequila, Citronge, sour mix, orange juice and club soda, a squeeze of lime, I now know; I ordered it without the descriptor). Then we head over to the Thirsty Mermaid, a quieter spot, for our first real salads (with shellfish!) of the trip. The night ends at Green Parrot Bar for live music, which absolutely slapped, and a Netflix movie back in our living room.
Sunday
9 a.m.: Roosters roam around everywhere, and I start my day with croque madame at the hotel restaurant, families quietly eating around us. We’ve booked a trip through the hotel with Sunset Watersports to go snorkeling and see some dolphins, and I want to make sure there’s enough in my stomach for being out on a boat, albeit in smooth waters, for a few hours.
11 a.m.: After yesterday’s rain, the perfect sunny day is welcome, and we set out with a little less than a dozen others on a small-ish motorboat. We’re marveling at the number of abandoned sailboats out in the water tied to dinghies, which we’re told is due to how shallow the water is here, and that the grasses are protected; they get stuck, but moving them can cost a boat owner thousands per square foot of damage, so they just eat the cost and let them rot until the coast guard goes through every so often and rescues them. We spot one dolphin splashing around, and then head out to get in the water.
I haven’t been snorkeling in ages, and forgot how wildly soothing it is to bob around and stare down at the sand. I spot a few colorful guys and a spiny lobster, and before I know it it’s time to get back on the boat.
There’s also a sandy stretch with chaise longues for relaxing.
2 p.m.: Once back on dry land, we haven’t had enough water time, so we get some snacks at a Cuban sandwich spot and head over to one of Key West’s only true beaches, Smather’s Beach, where the hotel has chairs. The water is super shallow, and there’s also an air show happening, so we wade out and stand with a bunch of others watching the fighter jets do tricks. It’s kind of amazing. (My sunburn the next day disagrees.) After a little more lying down, we grab the hotel shuttle back—included in the resort fees, we find these are nearly always booked, but got lucky this time—but not before spotting the plaque commemorating where Diana Nyad came out of the water after her historic Cuba-to-Florida swim. When we’re back, we sit by yet another pool with yet another piña colada.
6 p.m.: My friend remembers the sunset watch in Mallory Square vividly from a trip she took here in childhood, so, after a shower and a little reading on the sand outside our rooms, we head down to check it out. It really is quite a scene, and, dare I say, moving to be gathered with hundreds of others just watching the sun, as performers and tarot card readers attempt to grab a few dollars. But as soon as the sun’s down, it’s time to jet. For our last dinner of the trip I want a guaranteed good time, so we head to the Half Shell Raw Bar and feast on stone crab and various delicious sides. It’s gigantic, with whirring ceiling fans, and covered in vanity license plates.
Now that the weather is finally good enough, we’re excited to walk around more, albeit in the dark, checking out the beautiful homes, and a cemetery with a headstone shaped like a gigantic conch shell. My friend who smartly recommended the Green Parrot also told us about Bobby’s Monkey Bar, where they have karaoke every night. Sure enough, we walk in and the bartender is serenading fewer than 10 people.
The crowd fills out slightly, but the vibes are perfectly weird, right down to the middle-aged woman who appears to be a neighbor (and a regular) who pops in in a long cardigan and house slippers to perform a K-pop song. She absolutely slaps.
9 a.m.: We’ve timed our exit so that we can have one last breakfast by the pool and then a dip. Post-shower, we head out, the drive even more beautiful this time, making sure that we can squeeze in one last meal, an actually decent key lime pie slice, which we have yet to consume. We find it at the Key Largo Conch House, and eat it in just a few bites while watching a video—available for purchase!—of various shipwrecks near and far.
Sometimes you get a feeling of pure exhaustion after too many days at the beach (“I need a vacation from my vacation!”), and the strong urge to be home immediately. I’m so relaxed I can’t feel that (plus, my flight is on time, so there’s nothing to stress over). But I am pleased by how chill both resorts were; none of the craziness I anticipated (or feared) ensued. They might not scream “design destination,” but maybe that’s the point? The families weren’t too overwhelming; on the flip side, there were no club vibes in sight. Perhaps it’s because neither were true gigantic, Club Med-style experiences. Or maybe it’s the overall vibes of the Keys, which seem to refuse to tolerate much high-energy anything. My unavoidable sunburn still yet to fade, I’m realizing that “life’s a beach” when you’re at any beach, but the kind of life it is really does depend on where you are. At least slightly.