Long before hanging chads and headlines like “Lakeland Woman Treats 6-Foot Gator Like a Baby,” my splintered family shared a unifying dream: Florida, where true happiness was to be found among palm trees and miles of beaches. It was where everything would be OK. It was our promised land.
That may sound surprising. In an increasingly confused country, the Sunshine State is the place the rest of America always feels it can laugh at, because really, inside, it feels bad about itself.
Florida represents so much that’s good, bad and bizarre about the United States, all rolled into one long state. It’s where all of our sins go to be washed away by the ocean: drugs, shady real estate developers, and the Palm Beach County man who, in 2012, ate so many cockroaches and worms in a bug-eating contest (the prize was an ivory-ball python) that he vomited, collapsed and died.
It’s filled with beauty and contradictions. Legend tells us Ponce de León ended up sailing to somewhere near Melbourne Beach in his search for the Fountain of Youth, and grandparents go there to live out their golden years. It’s the setting for movies like “Moonlight,” and fiction by Elmore Leonard and Karen Russell and Laura van den Berg. It’s mysterious and beautiful, spooky and exciting. And yes, it’s weird.
One by one, my entire family moved there — first the grandparents, then the aunts and uncles. They loaded up cars and moving trucks with what they wanted to keep from their old lives and headed south. My parents followed, but I didn’t go. My father and I hadn’t talked since I was 12, my mother made the move from Chicago when I was 16. Estranged from both, I dealt with the Chicago cold as best I could. Not the most ideal situation for a teenager, trying to figure out how to make it on my own, but it sure beat living in Florida, I reasoned. The dream came true for them; I stayed back.
Eventually, in my early 20s, I would spend some time there when things got particularly rough. I thought I could escape and collect myself, that the beaches and blue skies would help me figure out what I was doing wrong — but I didn’t stay long enough to call Florida home. Worried I would never leave, I said goodbye, taking a bus from Broward County to New York, figuring I would never return.
Yet I still find myself going there yearly, sometimes for work, other times because I feel a longing for something familiar. Nowhere in the world has pulled me back so much. There is something I can’t shake about the place where the saw grass meets the sky.
I also discovered that Florida isn’t a monolith; it’s many states in one, filled with different people and cultures. When I was drifting in my early 20s, I made the daylong solo drive from Chicago to Palm Beach County.
Now, I fly into Jacksonville, the state’s largest city, and start my drive through a place I’ve never quite understood. A place that always felt like it was where people went and became lost to me. But I recently headed out on a road trip through Florida trying to figure it, and maybe myself, out.
Geographically speaking, Florida is as south as it gets. Yet its northern reaches are its most Southern. Moss hangs from the trees, the pace is slow and there are Confederate Army tributes in places like the Jefferson County Courthouse in Monticello. This Florida barely resembles the state we’re culturally fixated on: no neon lights or pink flamingos. Once you hit the highway, it’s horses running in big fields, miles of native pine trees and a lot of trucks.
I spend a good chunk of my drive to Tallahassee with the 2002 Mountain Goats album named after the city playing on repeat. “What did I come here for,” the singer John Darnielle wonders in the opening self-titled track, and I can’t help but ask myself the same question. It’s been over 15 years since I last visited this part of Florida; I was 19 and leaving behind a relationship.
For a place that’s home to three colleges, the state capital is surprisingly calm. As three locals in a row put it, Tallahassee is “chill.” Students make up close to 40 percent of the population, which usually means you can find a few good bars. So I do, stopping in at Waterworks, a tiki bar with waterfalls running over its windows. I order a Zombie and comment to the tattoo-covered bartender, Sierra — a city native who grew up walking past the bar and dreaming of working there one day — about how everything seems really close in the town. It isn’t small, just condensed.
“Everything in Tallahassee feels 15 minutes away,” she agrees.
Some parts of Florida feel as if time has passed them by. As I drive south, I pass old, rusted neon signs that once lured tired tourists 30, 40 or 50 years ago. Billboards on the side of the road proclaim, “When schools had prayers and Bibles they had no drugs,” above verses from Psalms and Matthew. Tourists can bypass these long stretches now, flying into the major cities instead.
I stop near Fanning Springs State Park and look out onto the Suwannee River for a few minutes. People talk about this part of the state as “landlocked Florida,” but the truth is that it’s hard to go anywhere and not find a body of water and just watch it for a little while.
My next stop is Gainesville, another town nationally known for college football, where the North and South slowly start to merge. I enjoy great grits and biscuits at the Flying Biscuit, and $3 Pabst Blue Ribbon tall boys and a game of NBA Jam at Arcade Bar. While the parts of Florida that brush up against the Atlantic and the Gulf of Mexico are notorious hot spots for spring breakers, in October, crowds descend on Gainesville to see countless bands play the punk rock festival known simply as the Fest (this year, Oct. 27 to 29).
Some punk attitude, however, sticks around all year. Gainesville has been called a “popular destination for homeless travelers,” and as I walk downtown, I find two men, no older than the legal drinking age — one with a shaved head, and another with a couple of nascent dreadlocks — hunched against a wall. I comment on a band patch one of them has sewn onto his pants. They ask if I can spare some change. I give them the three singles in my pocket.
They tell me Gainesville is great because it’s warm and the beer is cheap, “but the cops suck,” according to the one with the shaved head. I ask where they’re headed. “Somewhere in Georgia,” one says, but doesn’t specify where. The one with the dreadlocks tells me what he thinks of the local police; every other word is a profane one. The two men, like so many other people before them, thought they had found the perfect place. Like me, however, they are set to hit the road again.
Nestled between Tampa Bay and the Gulf of Mexico, St. Petersburg is “Florida’s Sunshine City.” From a distance, I see what looks like what could be a modern subject of a tropical Winslow Homer painting, sitting on a bucket, head down, sun-bleached cap covering his face, line in the water. I can’t tell if he is awake, but when he nods and says hello, I ask if he’s from around here. He says that he moved to Florida 30 years ago and that he hasn’t left the Gulf Coast since Sept. 11. He has everything he needs.
Here, the moss-covered Southern Gothic of the north turns to hand-planted palms. It’s the year-round home to the largest shuffleboard club in the world, which is just 15 minutes away from America’s oldest greyhound track and close to the first public jai alai fronton in America — remnants of an America that was fascinated by Florida’s possibilities after World War II. St. Petersburg, maybe more than any other part of the state, is a reminder of the Florida your grandparents dreamed of escaping to.
Nearby Tampa is the home of the Cuban sandwich; at least that’s what people from there will tell you. Although the sandwich’s exact creator and the location of its origins are debatable, the Ybor City neighborhood’s claim seems solid: that its large Cuban population, which swelled toward the end of the 19th century, at least popularized the idea in the United States that combining ham, roasted pork, Swiss cheese and pickles between bread is a fantastic idea. I eat one at the Columbia Restaurant. Opened by a Cuban immigrant in 1905, it takes only a few bites for me to admit that Tampa has a convincing argument.
I do more walking around Ybor City. Through headphones, I listen to the Hold Steady’s “Killer Parties” on repeat, Craig Finn singing about how the neighborhood “is très speedy, but they throw such killer parties.” I stop in at the Bricks, a cafe and bar, and drink a beer at one of its sidewalk tables. With one whiff I can tell why the place is called “Cigar City,” as people all around me are smoking hand-rolled stogies. I look around and, for the first time on my trip, feel as if I’m in a place where I could see myself living.
Maybe no part of the state takes the brunt of Florida-directed abuse quite like Orlando and its surroundings. A woman sitting next to me at Stardust Video and Cafe, a coffee shop/video store/library, laughs and states the obvious: “I blame Mickey Mouse.” Yes, living in and around the center of tourist hell is, as a number of locals told me, strange. Yet Orlando and its surrounding area, especially the city of Winter Park, can surprise you.
Take Wally’s on Mills Avenue in Orlando, a bar inside a liquor store that proudly states on its website: “It was here before Disney, it was here when Orlando was nothing more than a stop on your way from one coast to the other.” It’s slow when I’m in there, and I have to drive back to my hotel, so I have my drink and leave. I go to my hotel room and do something I haven’t done since high school: I pick up a copy of Jack Kerouac’s “The Dharma Bums.”
Kerouac has Florida connections. He died in 1969 at 47 in St. Petersburg, but a decade earlier, in a little blue house, right before Walt Disney came scouting land for another theme park, Kerouac wrote “The Dharma Bums” in Orlando. I drive past the unsuspecting little house on Clouser Avenue and wonder what led Kerouac to this place. It’s a town that, at the time, didn’t really offer up much of anything. I can’t help but think that maybe if you spend enough time in Florida, something inspires you. Maybe that was my problem all along: All I ever wanted to do was leave.
To get to Palm Beach, you can take either Interstate 95 or the Florida Turnpike. There isn’t much to look at along either route, and as my phone’s connection drops out, I find myself fiddling with the radio. I hear preachers, then Spanish, then Haitian Creole, and more preachers as I inch closer toward Palm Beach, a stop I’ll be skipping because the president is in town, playing golf at his winter White House.
I head down 95 until I hit Boca Raton, which has some of the most expensive gated communities and homes in the country. My grandma moved to an underdeveloped part of the city in the late 1980s, then watched the strawberry fields she could see from her window uprooted to make room for more buildings. “Boca’s Boca” is all she would say.
Like countless others, my grandparents made their way down there, first as wintertime visitors, then as full-time residents. Both of my grandfathers, who were so happy for a short time after they traded the weather and problems of the North for their new home and their new lives, died within a decade of making the move. That thought crosses my mind as I pump my gas and decide that Boca doesn’t hold anything for me.
Farther south down the highway, Miami, on the other hand, does have plenty I want to experience. For all of the misconceptions people have about Florida, Miami tends to escape scrutiny. Sure, it has long been pegged as the cocaine capital, largely thanks to movies and television shows, but it also has a special international flair.
Before I go to my hotel, I drive downtown, past the old Freedom Tower building. Constructed in 1925, it got its name in the 1960s as the place where Cubans fleeing Castro were taken to be processed and documented. Today, it houses an art museum (closed until next spring). Nearby, they are building the One Thousand Museum, designed by Zaha Hadid, the future crown jewel of the neighborhood. Miami is in the middle of another building boom, despite rising sea levels.
But life goes on. For now, there are always neon lights flashing and Pitbull songs playing somewhere. Both, in fact, are happening as I sit down at the poolside bar of the retro-kitsch Vagabond Hotel in the Mimo district. In my first hour at the bar, I also hear Spanish, Arabic, French and plenty of Long Island accents, and talk with a young Japanese guy who tells me he moved to Miami because he’s a graffiti artist.
The Wynwood neighborhood was desolate when I stayed in Miami in my early 20s. Now it’s covered in art, spray-painted on the sides of galleries, restaurants and boutiques. I feel particularly at home at Gramps, with its pinball machines, large outdoor space and DJs spinning a blend of West African funk and Italo-disco.
Key Largo was the setting for and the name of Humphrey Bogart and Lauren Bacall’s last film together. Bogey’s ghost retired here, perhaps drinking a beer at the Caribbean Club, the “poor man’s retreat” that opened in 1938 and was used as a location for the film. At midmorning, it’s a mix of bikers, leather-skinned fishermen and two guys who look as if they’re staying at the Yacht Club, their Vineyard Vines shirts a match for their pink skin.
Driving through the Keys, I pass island after island, as well as the famous Seven Mile Bridge. The ghostly Bahia Honda Rail Bridge comes into view in the distance. I think of the Keys travel book that Joy Williams wrote. She is best known for her fiction, but I picked up her 1987 history and guidebook, and it set up my last leg of the trip nicely. Her words about the abandoned structure echo in my head — “it is said that Henry Flagler loved concrete with a passion,” and that the sheer size of the project proved too daunting for his young engineer at the turn of the century who “literally worked himself to death on the project,” a year into construction.
I make it to Key West and pull up to a bungalow. I’m greeted by Mark Straiton, whom I know as Cowboy Mark, a guy I met years ago somewhere on the Lower East Side of Manhattan. He is an old friend, someone I made sure was the last person I’d get to spend time with on my trip.
We were both younger and drunker when we first met. He wasn’t an actual cowboy, as far as I knew (he is from Connecticut); that’s just always been his name. Mark’s New York City life saw him in bars that aren’t around anymore. He looks like a hoodlum from the 1950s, all tattooed up, dressed head to toe in vintage denim. After so many nights closing down bars, Mark made his way down to Key West. Like so many before and after him, he stayed.
“I told my boss I wanted a full-time job and he told me I had to live here a year first,” he tells me as we walk, beers in hand, past police officers who pay us no mind, by Books & Books, an independent store the author Judy Blume opened in 2016, and a vendor selling a dozen different Jimmy Buffett T-shirts.
Mark waves at or shakes hands with about a dozen people. It feels as if I’m in the middle of a sitcom, all of these sun-kissed Floridians who escaped from somewhere else, only to end up in Key West. Some just wanted to live near the ocean; others, as Mark explains, were leaving behind addictions and bad relationships. Everybody here knows your story.
As Mark tells it, there are two kinds of Key West locals: the ones who will be gone in a few months, and the ones who end up there thinking they will be in that first group but get really comfortable and don’t leave. We stop into Mary Ellen’s, a neighborhood sports bar with a beautiful collection of vintage beer cans mounted on the wall like a museum exhibit and a menu that boasts the “best fries in town,” which I can’t really argue with.
It’s about 1 in the afternoon, and we’re joined by about five other people at the bar. When I ask them if they’ve been to my main destination, the Ernest Hemingway House, one of them takes a drag from her vape pen and tells me her boyfriend made her go — she was hesitant, but was charmed by the cats.
After a visit to the cats at Hemingway’s house, where the 20-plus six-toed animals are truly just as much an attraction as the Nobel Prize winner’s home itself, we end up walking toward the water, to the beloved Chart Room, a dark and dirty little spot where Mark tells me the “real locals” hang out. We walk up, and it’s not open. “I honestly didn’t think this place was ever closed,” he says. “I don’t know where the regulars would go.”
We end up getting a beer at a place packed with tourists, and before I say goodbye to Mark, I consider asking him if he ever thinks he’s coming back to New York City, but I don’t. I miss him and our weird nights, but I also realize he seems as if he has found some peace, he’s happier. Why would he want to leave?