A Roadtrip on the Overseas Highway

Sitting between the Atlantic Ocean and the Gulf of Mexico are 1,700 islands that comprise a region unlike any other in the United States. Marc Smirnoff says goodbye to Miami and heads to the Florida Keys.

If on a map, Florida takes the shape of a ballet slipper executing the classic en pointe, then the Keys are a wisp of thread stirred up by that move.

The Overseas Highway covers that wisp with 126 miles of concrete. Were it not for that skinny road and its 42 bridges, the Florida Keys would, literally, not be attached to—or united with—the contiguous U.S.A. Talk about an outlier! And once you leave the Florida mainland by car, the two-lane Overseas is the only way to Key West, which lies at its end. One lane leads in. One lane leads out. Simple. Direct. Primal?

The last outpost on the mainland before crossing over to the Keys is Homestead, a typical cityscape of traffic and malls until, that is, the road abruptly narrows and is separated by a formidable traffic divider, painted blue. And then from each side, and giving off a federal prison vibe, tower barbed-wire fences, painted black. Surely this couldn’t be the paradisiacal Keys?

Though I want to stop and check a map, I ride on. It’s not like I have a choice. In my one lane of slug-like traffic, there is no space for stopping or turning back. It’s the same from the other direction. Beyond the barbed wire are glimpses of swampland and vivid swatches of water on both sides to tease the eye. Topping it off is an expanding blue of cottony-cloud sky. I know because my rental—a black, Burt Reynolds-cool Camaro—has a sunroof. When I finally see a (rare) turnoff for something called Manatee Bay Marina, I know this is the Keys, unwelcoming or not.

I’m cruising to Hawks Cay Resort (rooms, from $200; 61 Hawks Cay Blvd.; 877-484-9342), smack in the middle of the Keys in Duck Key (mile marker: 61.1; population: 621).The first town past Manatee Bay Marina is Key Largo, which is clotted with ads for souvenirs, beach garb and close encounters with animals. My favorite: “Feed and swim with sharks!” The main drags of the other towns on the highway exude a similar theme-park desperation. But it doesn’t matter. Whatever is manmade here is diminished by the exuberance of the outdoors: by the plush plant life; by the moody, impulsive skyline; by the royal Atlantic Ocean (on your left as you head to Key West); and by the majestic Gulf of Mexico (on your right).

For anyone stuck in the heavy metal and constant jamming of urbanism, the fluid, soothing beauty of the Keys creates new dulcet notes.

When I arrive at Hawks Cay, it is just before dusk, and I am sleepy. But I push myself outside to walk the residential streets. The air is an uncanny mix of warm and cool, and, to my surprise, I can’t stop looking at the trees. Trees on the mainland stand with firm dignity; trees in the tropics dance; they poke, beckon and twist.

Then there is the sunset. Many of the articles and books I read before embarking on this trip repeated a variation of “Be sure to check out the sunset here”—and then name a restaurant or bar that offers the “best” view. But nothing has prepared me for what the sunsets do.

I amble into a tiny cove that looks like a dirt parking lot. A gap in the surrounding foliage gives a view of the water, which is where I’m headed when a three-wheeler carrying a dad and a mom and a little boy beat me to the front row. Dad, a Keys native, says his family often comes here at this very time to watch the sun.

Then it begins: A mixture of red and orange layers flares from the horizon and veils us, veils everything, in radiance. The mom says, “No paycheck gets you this.”

Two cars pull up. The dad on the three-wheeler says, dejectedly, “There’s never anyone here,” and they take off. A family falls out of an SUV and lines up in the vacated spot, facing the cinematic horizon. Hoisting their cell phones over their heads, they hold steady to take photos and video. You can see the awe in their eyes. I imagine they would look very much the same, down to the cell phones, if the sky, instead of a sunset, were revealing a UFO or the Virgin Mary.

The gold light continues to illuminate and bathe the cove and everything in it, our hands, our fingers, the pine needles, the ground. If I am counting right, this goes on for 15 or 20 minutes.

It baffles people when I tell them my assignment is to visit the Florida Keys but not Key West. The rest of the islands are often viewed as mere stepping-stones that lead you to bustling Key West. But outside Key West you will find islanders who take pride in having little to do with that town. All I know is that the entrance to Key West, which I drive to the next day, is crammed and cluttered with more fast-food outlets and more combative signage than I’ve seen anywhere else so far. An entrance is not a fair way to judge a place—surely there are treasures within!—but I am relieved to do a U-turn and retrace the 60 miles of quieter scenery that coax me back to the Middle Keys.

Back in those Middle Keys, in a parking lot in Marathon (mile marker: 53.1; population: 8,297), I approach two cops who are nearby talking. The idea hit me last night that no local or expert would know a place more intimately than a cop. Here is my chance to test that theory. One of them wears an army-green uniform; the other a more typical police outfit. Both sport hefty sunglasses.

As I walk up, I can tell their eyes, even behind the shades, are on me in that cop way. I say, “Excuse me, gents. I’m on a writing assignment and was wondering if you could recommend a place to eat?”

The cop in army-green answers. He has the heft of a linebacker and says, “I could name two restaurants that are well known—and on the highway. But there’s Paradise Juice [2603 Overseas Hwy., Marathon; 305-735-4051], a place run by two Cuban sisters that only locals know that I think you might be more interested in.”

Kind of uncanny. It’s the sort of tip I dote on. Maybe the guy knows more. So I ask him what I should visit inside Marathon (“the turtle sanctuary”) and how safe the area is (“pretty safe”; the slow highway repels criminals who prefer fast getaways). We keep talking until the other cop walks off. Then the one left says something that jolts me: “If you really want to see the area in a way that most people don’t, you should ride with me on my boat while I patrol.”

The abandon with which I shout “yes” is loud—and childish. He’s a boat cop! I sign, but don’t read, a release form. Ain’t no legalese gonna stop my police-boat ride. And we drive to the city marina, where the boat is moored. I’m not one of those he-men who can tell you about mechanical stuff (I’m a different kind of he-man), but the two outboard motors on the sporty police boat are the size of phone booths. I am given a life jacket and advice on where to move myself should we start taking bullets (behind a slab of Plexiglas), and we’re off.

When the cop tells me to hold on, I think he is being officious, but after he jiggles the hyper-speed knob, I am grateful for the tip, because we burst forth in a neck-snapping fury that feels like it really wanted to toss me into the water. Suddenly the visible world blurs, and I wonder if this is what it’s like to be on LSD with an officer of the law.

As we hurl forward, the warm air, whipped up by the ferocious speed, presses sweet against me like a masseuse. Even the freshness in the air soothes. And then there is the “beautiful blankness” of the sea, as John Updike saw it. All these elements, and probably others, work together to lure me into a kind of trance, a kind of bliss.

To go underneath the Seven Mile Bridge in Marathon, we abruptly lose speed, and I wonder if this is what an astronaut feels on returning to the routine of the earth’s atmosphere. The most fundamental things baffle me now. From below, the columns that hold up the bridge are so massive as to seem otherworldly. Maybe I can ground myself by learning a bit about the cop—like his name, for starters.

It’s Wilfredo “Willie” Guerra. Of Cuban descent, Willie was born in Chicago but moved to Miami at age two. He is married and lives with his five children in Marathon in a house on hurricane-sensitive stilts. Unlike some policemen, Willie is not dour or terse. Rather, he’s been upbeat and chatty from the get-go.

I ask him what he does with his free time. “I get out on the water,” he replies. “Go boating. Or fishing. Or diving. And spearfishing.”

When our joyride is over, I can’t stop thrumming—and smiling. I ask Willie to help me understand why the Keys are having this effect on me, and he answers with a kind of riddle: “A lot of people who live elsewhere? Maybe where they live has a few focal points. But what are they? A few buildings and that’s it.”

Now he’s Lenny Bruce with a badge. Later I won’t be able to stop thinking about Willie’s quip. He’s suggesting that some of us live in nice-enough locales where uppity nature has been knocked around, pushed aside—and segregated, if not outlawed. And so we genuflect­, not to nature, but to edifices. Edifices where some historic bill was signed or some historic figure grew up. Willie and the islanders, meanwhile, romp about in what we could call the museums of the wild, and the aesthetic nourishment that they breathe in, direct from the source, is something that we, on the mainland, barely get a hint, or whiff, of.

So far, I’ve enjoyed two charmed playgrounds: Hawks Cay Resort and Cheeca Lodge & Spa (rooms, from $230; 81801 Overseas Hwy.; 305-664-4651), in Islamorada (mile marker: 81.5; population: 6,119). But Moorings Village and Spa (rooms, from $350; 123 Beach Rd.; 305-664-4708) might be the most enchanted. Even its overgrown jungle of a parking lot has me gobsmacked. When I say as much to blonde, athletic Bryanna, the Moorings employee showing me around, she says, “It’s funny you mention that. Nintendo filmed the jungle backdrop for a Donkey Kong commercial here.”

Turns out cameras are often on-site. By only a few days I’ve missed playing volleyball with Sam Shepard, Sissy Spacek and Kyle Chandler, who were filming an upcoming Netflix series at the Moorings. They’ll be back after I leave.

The shooting frenzy began in the mid-’90s, when the photographer Bruce Weber (see Necessary Luxury, page 264), a pal of the owner, got it in his head to take a portrait of a model and an elephant on the Moorings beach. From then on, it seems every big-name snapper has finagled a gig here. It’s easy to see how the sensual beach and the scene-stealing foliage and the airy cottages appeal to even non-photographers.

The owner eventually accommodated the photographers even more by building a studio for them. From the outside, it isn’t much, a garage or warehouse. But when Bryanna opens the door, I see a room so enormous and so white—even the piano is painted white—we could be in the Wonka Factory or a snowstorm. Except, well, for the fake and multicolored bedroom suite against one wall, which I somehow don’t make a wisecrack about, and a mass of framed magazine pages and covers featuring photos that were shot at the resort.

Later that night I head across the highway to the Morada Bay Beach Café (81600 Overseas Hwy.; 305-664-0604), which, along with a restaurant called Pierre’s (81600 Overseas Hwy.; 305-664-3225), constitute the Moorings Village empire.

I get a table outside on the beach. Next to me is personable Brittany, whose job tonight is seating people. Brittany, a native of the Keys, goes to school in Miami but returns home in the summer. I ask her to compare the Florida mainland with the Keys. “South Beach in Miami is very cool—for a day or two,” she says and admits she's afflicted with “The Keys Disease,” the tag locals give to the condition of being silly in love with the place.

She also tells me that the area’s “island girls” are not to be confused with the chicks who come to Florida to tan. Island girls are athletic and keen. For them, the water is not a backdrop; it’s for using. They use it to boat, to fish, to snorkel, to dive and they do so constantly.

Hearing this, I now know that I’ve been among island girls without even realizing it. Not only is Brittany an island girl (“It bothers me when I don’t get on a boat for a while”), but Bryanna, my guide at Moorings Village, is, too: She boats, fishes, dives, snorkels—all of it. As are others I met. A tidbit: Every one of these island girls I’ve met spearfishes. Until this visit, I had never even met a man who did that.

Later I saunter next door to Pierre’s, which is rumored to be the swankiest eatery on the Keys. Tonight is ladies’ night. The bar is one of those classy, dark-wood affairs. All around is piquant art, including a signed print of Bruce Weber’s elephant/model shot from just across the street and an old-school crew boat fastened to a wall. But ladies’ night? All I see are a few married-looking couples at tables and three guys in the corner on couches speaking a foreign tongue. When I realize I’m bored, I decide to interview the three guys, who must be tourists. I introduce myself and ask if I can pepper them with questions.

There’s silence until, at last, one of them says: “Sit.”

Their accent turns out to be French, but all three now reside in Islamorada. The ringleader, the one who invited me to sit, is David (pronounced DAH-veed), who has lived in the Keys for three years. Even though it’s balmy outside, David, a tanned, thin, courtly man in his forties, is draped in a scarf that touches his knees. He’s arrayed in a well-fitting shirt with a few buttons open, a sleek necklace and funky yellow glasses.

When I ask him what he thinks about the Keys, we get lost in a twisty but stimulating theory about how the region will soon—and definitely—become the next Hamptons or Montauk of Miami. At times, David can sound like a French Andy Warhol: “The Keys were way ahead of their time, and now time is getting in time with the time.”

I actually buy his argument. When places are extraordinary with beauty, or with some obvious attribute, the rich take over. I saw it happen in Mill Valley, California, and later in Oxford, Mississippi. And neither of those towns oozes the grandeur of the Keys.

He says a few times: “To live here, you have to be a millionaire.”

Maybe it’s the tricky accent, but to my ears he’s implying that’s a good thing.

Real estate on the Keys is already beyond most people. But that doesn’t mean the Keys can be defined by money. Even in my quick time here, I’ve been struck by the compelling and soulful islanders I’ve met who somehow manage to thrive on low wages as waiters, animal caretakers, interns, etc. They tell me they live poor because they want to be or need to be here. Basically, they have that Keys Disease, which is not synonymous with the love of money.

So I argue this point with David. But he does not budge. Finally, I say, “Well, David, if you have to be a millionaire to live here, and you three all live here, that means I’m surrounded by three French-American millionaires. Is dinner on you?”

David: “No. No. I am not. You don’t understand….”

We waltz around like this for long minutes, dizzying ourselves.The other two watch our performance in silence.

Theory usually repulses me, but when I relax and accept their groove, David’s words begin to sway and enlighten me. We end up talking for a few hours. About the Keys, he says, “You have a freedom here that is priceless.” And “if you don’t use the water here, you have an issue.” And “money should not be a corruption; it should be an enjoyment.”

We walk outside for a smoke and more chatting. A man and a limping woman brush by us. The woman has glowing eyes. A male would want to swim in them, but I turn back to David. Then I hear her ask me, “What kind of camera is that?” And that’s how I meet Donya and Mark. Both are natives. Mark, a bulky fellow in his forties, has a Keys tan and still lives here. Donya, also tanned, is a lithe, short-haired sprite. She is visiting from Los Angeles. Actually, she flew in from Scotland, where her best friend, the Baroness Kelly Cooper Barr, got married in some castle and where she, Donya, tore some kind of leg muscle while dancing to the wedding music, live, of either Duran Duran or Simon Le Bon (we never got it straight). Outside of some genius children, Donya is probably the most in-the-moment human being I have ever met. If you take your eyes off her, she is jumping to catch the whirling blade of a ceiling fan or perilously balancing on a banister.

Donya’s a photographer who also just wrote a children’s book for Simon & Schuster. At age 14, she began to model and eventually posed for Maybelline and Pepsi. “I came in second in 1985 as Miss Teen All American. Halle Berry was first,” she says with a laugh.

Mark and Donya met in their teens. Their banter reveals, among other things, that Donya is all island girl. Perhaps its source. Growing up, she fished, snorkeled, dove, boated, swore. And when she’s back here? She does it all over again.

Mark and Donya lure me to a late-night dive, the Oceanview, or as they call it, the OV (84500 Overseas Hwy.; 305-664-8052), which is packed—with locals, I think. Half of the action is happening inside, half out. Donya points and shouts: “There’s Bobby! Bobby Rogers! My first crush!”

Bobby is huddled in a corner, and when Donya reaches him, they hug and catch up. Eventually, I find a moment to quiz Bobby about an earlier claim of Mark’s.

“Is it true that Donya water-skied to school?” Bobby laughs and says, “Hell yes, it’s true. Every day.” Me: “Was that normal? Did you all water-ski to school?” Bobby: “No. I mean, I boated to school. Most of us did. But only Donya water-skied to school.”

Then Mark says to Bobby: “Hey. Remember how we used to catch sharks? And keep ’em at the beach where Pierre’s is now? And sell ’em live to the universities? For their laboratories?”

Bobby: “Sell ’em live? I sold mine dead. And I sold them.”

And they argue—not about whether they actually caught sharks back in high school—with their bare hands—but how they sold them.

The next night is my last one in the Keys, and I return to Pierre’s to meet again with Donya and Mark. High jinks ensue. At one point, I go out to the porch by myself, where I see a fellow tourist I’ve been evading, a young cigar-smoking dude who’s been boozing it up and boasting about all the money he’s been making of late. Now he has cornered David. Neither of them notices me.

The kid is clearly thrilled to be in the Keys, and in Pierre’s, and you can tell he wants David to like him. I’ve learned, by the way, that David is director of operations of both Morada Bay restaurants. But David didn’t tell me. The night before, when I asked him what he did for a living, he slyly answered, in that French way of his, “Let’s just say...entertainment.” Because the drunk kid is loud, eavesdropping is compulsory. Here is my memory of what the drunk kid says to David: “Man, we got it worked out. We find these distressed businesses, and, BAM, we swoop down on them and we make so much, man. I’m not even kidding, dude. If you want to invest a few thousand—and I can guarantee it—you will get, in just one month, a return of—” And he rattles off an indecent figure.

David responds with words I can recall verbatim: “I don’t invest in failures. I invest in success.” And with that, David, with grace, turns his back on the guy and leaves the porch.

As I seep into my fifties, I dream that honor exists in our world; that there are people we don’t hear about who aren’t for sale, and even when they think no one’s watching, can’t be bought.

Driving out on Overseas Highway the next morning, I watch an iguana the size of a Shetland pony materialize in front of my car. This is my second iguana sighting. Verily, the wildlife of the Keys, on land or off, can overwhelm a visitor. Twice I’ve seen dolphins when I was out walking by the water.

The last time was on a beach with just a few other people around. Suddenly, three dolphins curved out of the water in unison, like an impromptu circus act. One person wading in the water had his back to this show, but a father and two kids next to me happened to be looking out, like me, and our transfixed eyes stayed on the horizon long after the dolphins had vanished.

Anyway, now there’s this Florida Keys iguana to contend with. Though he looks like he could spit fire, the little dragon does not lunge at me or the bumper. In fact, as I slow down to let him waddle to the side, I realize that the iguana doesn’t even notice me.