“As far back as I remember myself (with interest, with amusement, seldom with admiration or disgust), I have been subject to mild hallucinations.” ~ Vladimir Nabokov
THE FIRST TIME I REMEMBER feeling like a fish out of water was age five. My family had just moved to Nashville from Newport Beach. Up to that point, all I’d known about life was a Southern California idyll, where purple and white wildflowers carpeted the bluff outside the sliding glass doors of our little condo on the Back Bay; where the cold, dark blue Pacific Ocean foamed against the golden sand of Corona del Mar’s beaches; and where the tan leather seats of my mother’s Volvo station wagon would, after sitting in a parking lot in the blazing sun, either swaddle us in warm comfort or singe the flesh.
But maybe all those memories came later. Maybe those memories are from my early adolescence in Newport after we moved back from Nashville two years later and into that same condo on the bluff.
All I know is that it was in Nashville where I first felt like everything around me was strange and unknown. We lived in a little yellow house in Franklin where my mother planted pretty purple, pink and fuchsia wild-looking flowers on the pathway between our front door and the sidewalk. We had a black and white cat named Oreo who had two litters of kittens. Newborn, tiny and helpless, mewing with their eyes still closed, they were the most precious things I’d ever seen. We had a yellow aluminum swing set in our backyard where I played with our next door neighbor, Will, a boy with white-blonde, curly hair who was a grade or two older than me. I found his Southern accent, with its googly peaks and valleys, bewildering. I remember asking him, innocently, curiously, sincerely, “Why do you talk like that?” and “Do you know how to say YOU ALL?” emphasizing the autonomy of the two words as opposed to that elided staple of Southern dialect, y’all. Depending on the day, I was either infatuated with Will or infuriated by him. I guess he was my first crush.
Today, when I talk to people about where I’m from and where I’ve lived, I tend to skip over the Tennessee chapter. It’s easier to think about my childhood as one unbroken scene set in Southern California without the two year gulf in Nashville. It’s also easier for storytelling purposes. Too much moving around and you lose the plot. Better to boil it down to the essentials, the broad strokes. After all, Nashville was such a tiny blip in my young life, how formative could it have been? The real rupture came later, at age thirteen, when my family left California for good, moving to Alabama and then two years later to small town Georgia where my parents still live today.
But the truth is, that herky-jerky sense of uprootedness and foreignness has been a part of me for as long as I can remember.
And it started in Nashville. The place where I saw mystifying snow for the first time, my mother wrapping plastic bags around my shoes, so I could go out and play; where I performed the Back Porch Ballet, departing from the classical technique I was learning in ballet class in favor of my own original choreography; where my mother would gun it over Tickle Hill on the country road leading to our babysitter’s house, catching air for a delightful tickle in our bellies; and where, on the swim team, before becoming a strong blue ribbon-winning swimmer, I nearly drowned from nerves in my first meet.
At least I think it was in Nashville where all of that happened.
AFTER COLLEGE AT THE UNIVERSITY of Georgia, there was only one direction to go: into the great unknown. I had no hometown to return to. Sure, my parents were only a couple of hours away in Cartersville where I finished high school, but it had never felt like nor was going to be my home or the home of either of my two younger siblings. I would always have a longing attachment to Southern California, but my family didn’t live there anymore. So, armed with degrees in drama and sociology, and a vague desire for a creative life and to do some good in the world, I moved to New York City. I took a job as a middle school teacher with Teach For America, a national teaching corps with a mission to close the achievement gap in underserved communities.
My first year in New York—living in a tiny, crumbling apartment with two roommates and a mangy cat on the upper-Upper West Side, sandwiched between, yes, Central Park, but also a housing project; commuting to the far reaches of the northeast Bronx before dawn on a train, a bus, a train and another bus, then a long walk down a hill for a job I was barely qualified to hold; falling into a deep seasonal depression during a bleak winter when the sun began to set at 3 p.m. and the temperature in January never cracked 30 degrees—was the hardest of my life. But I made it to the other side. And I eventually came to love both teaching and New York City.
Summers were a revelation. I still got a paycheck, but I didn’t have to go to work. I was free to pursue my interests in the greatest city in the world. I took creative writing classes at Gotham Writers Workshop and an arts education course at Lincoln Center. I caught as many Broadway shows as possible with discounted rush tickets. I learned how to sail on the Hudson River and turned my sailing instructor into my boyfriend. I became one of Manhattan’s most notorious party girls—at least in my mind and the minds of my girlfriends as we charmed our way into the nightclubs of the Meatpacking District and West Chelsea night after night.
If my family’s leaving California when I was thirteen was a turning point, forever changing the trajectory of my life, then that first summer in New York was formative in shaping my philosophy on living. I had moved into my own studio apartment, a sixth floor walkup on the Upper East Side. This newfound taste of autonomy coupled with two months of funded summer vacation to live as I pleased was intoxicating. I began to fantasize about how to spend that time in the future, forget about teaching summer school.
By the time my second summer rolled around, I’d concocted a novel plan. It revolved around a catamaran in Key West that I’d first sailed aboard on a family cruise vacation when I was fifteen. I can still feel the sensation of plunging into the cool, clear waters, miles offshore, where the Gulf of Mexico meets the Atlantic Ocean, from the deck of that catamaran for the first time. I spied an enormous midnight blue parrotfish right away. Then, a mellow, grey nurse shark flitted by along the seafloor, startling me, but only for a moment because it swam off indifferently in the other direction and disappeared from sight. There was a loggerhead sea turtle plodding lazily towards the surface, purple sea fans waving in the current atop coral canyons and schools of yellowtail snapper, sergeant majors and blue tang darting this way and that, hunted by the occasional menacing-looking barracuda with its underbite of jagged teeth. Of course, now I’m conflating sights from the countless times I’ve since flung myself from the side of that boat and into the underwater world, but my devotion started with that midnight blue parrotfish.
On that first trip, on the sail back to shore, exhilarated by the warm sunshine and cool saltwater on my skin, I studied another captivating species. The crew, with their tan, broad shoulders, sun-bleached blonde hair and dark sunglasses, wearing only red board shorts, bounding about the deck, coiling lines, lifting heavy equipment and pouring beer. “Why don’t we get drunk and screw,” a voice sang over the sound system accompanied by loopy acoustic guitar, mingling with the gentle headwinds. I’d never heard the song before, but somehow I knew it was Jimmy Buffet and I loved it immediately. It was illicit and funny, delighting my still virginal ears; it felt like a promise of things to come. I soaked in the scene—the sun, the sea, the boys. This was paradise.
Perhaps that was the afternoon that changed my life forever because from that moment on, I thought to myself, “I want to do that one day.”
A few years later, to celebrate college graduation, I sailed with two girlfriends to Key West on another cruise and, of course, I went snorkeling aboard that catamaran again. This time, I asked one of the mates how he got his job. And he told me, “It’s easy. We’re always hiring—especially girls.”
It was a piece of career advice I never forgot.
I LANDED IN KEY WEST for the month of August between my second and third year teaching. I marched directly to the marina where those catamarans were docked and was hired on the spot. I had sublet my studio on the Upper East Side to a handsome law student in town for his internship and, in doing so, traded a summer of potentially meeting an appropriate mate like him—educated, ambitious, normal—for the siren song of bohemian Key West.
I rented a little cottage on a compound in Bahama Village with a swimming pool. I spent my days aboard sixty-five-foot catamarans, learning the ropes, swimming in the sea, pouring beers for tourists in my bikini and watching the sunset under sail almost every night. On my days off, I wrote on my covered porch, sipping mango juice. I read Hemingway floating in the pool and drank with the crew on Duval Street. It was the most fun I’d ever had. My month in Key West came to an end as Hurricane Katrina unexpectedly ripped across the island as a Category 1 storm before wreaking havoc in New Orleans—and with a love affair, which would ultimately prove nearly as destructive.
Back in New York, I dreamed about Key West every night. In those dreams, I’d spot one of our blue catamarans on the Hudson River, larger than life, framed by a romantic gibbous moon, grossly out of place against the backdrop of the city’s grey workaday doldrums. I wanted nothing more than to be on that boat sailing back to Key West. On the express bus to school every morning, I read Moby Dick and found, just as Ishmael had, that on the island of Manhattan, “right and left, the streets take you waterward.” And that’s where I’d find myself every chance I had, transfixed in my own ocean revery, like one of his silent sentinels. At the end of the school year, just as Herman Melville had done before me, I traded my job as a schoolteacher to become a sailor. I moved to Key West.
While everyone else I knew was laying the groundwork for careers, marriage, children, real life, I spent the second half of my twenties in Never Land working on boats, writing a novel and partying on Duval Street with the Lost Boys. Key West was freedom. All timetables were cast to the sea—except for what time the boats shoved off the docks. A Tuesday was no different from a Saturday and who knew—or cared—what time of year it was when the weather was almost always sunny and seventy-five degrees. Writing and sailing struck the perfect balance for me: a few days of quiet contemplation in a world of my own creation and a few days laboring in the hot sun with the boys on the boats.
And then there were the wild nights.
Years after leaving Key West, arriving to Venice Beach for the first time, I was overcome by a sense of familiarity—the boardwalk with its chaotic energy and crazy characters was like Duval Street on steroids, yet this was the Pacific Ocean, the ocean of my childhood, with the same tall, spindly palm trees, golden sand and dark, cold ocean—and it dawned on me that Key West may have been a subconscious reclamation of my lost Southern California adolescence. Those cute boat boys in red board shorts were stand-ins for the surfer dudes, swim coaches and water polo player crushes of my youth.
I once accidentally told someone that I was from Key West. That was the moment I realized that the island feels more like my hometown than anywhere else I’ve ever lived. It still does. Key West will always be a safe harbor for my wild soul to dock.
SOMETHING UNEXPECTED HAPPENED MY FIRST year in Key West. I saved money. Of all the reasons I moved to the island, financial solvency was not one of them. Nor was climbing any kind of “corporate ladder.” All I wanted to do was sail, swim at the reef and watch the sunset every night. But I was handed the opportunity to work on the parasail boats. If you’ve never worked on the water in Key West, you might not realize that there’s a hierarchy and a parasail mate is one of the most coveted and lucrative jobs available. You work shorter days, one-on-one with your captain, and leave the marina in time for happy hour with your pockets overflowing with cash. Suddenly, without really trying, my tip money added up.
As my first year in Key West drew to a close, I considered returning to teaching and some semblance of a normal life. I applied for a job at a charter school in San Francisco and received an offer. But visiting that school, at the end of a two week road trip up the Pacific Coast Highway with my best friend in a red Mustang convertible, I realized there was no way in hell I was returning to the classroom after the freedom I’d tasted in Key West. Besides, I had a better idea.
I had started writing a novel and I’d always wanted to spend more time in Paris. Winter was our slow season on the water, so buoyed by a cash reserve I’d never before possessed, thanks to my parasail tips, I took off for three months. I rented a tiny flat on the top floor of a seventh floor walkup (six French floors—they start counting one flight up in Paris!) where the hallway lights on a timer would sometimes flick off before I finished my hike to the top. It was on the Seine, on quai Saint Michel, where I could just spy the tops of Notre-Dame’s bell towers through my windows inside a building where my landlord, a sociology professor at the Sorbonne, told me Matisse had once lived. I slept on a single futon on the floor surrounded by walls lined with books in French.
I spent my mornings writing and my afternoons winding through the streets of Paris, following the ghosts of Hemingway, de Beauvoir, Sartre and Durkheim. I visited the historic fashion houses, the cafés and the great museums. I met girlfriends for Champagne—I went to Champagne! And I found love with a sweet, funny, handsome man from the Alps who took me skiing in his hometown. (By the time I returned the following winter, he was no longer mine.)
One afternoon, during that first winter, I sat at a café near the Panthéon, sipping a café crème, gazing at an enormous banner rippling down its façade that read AUX GRANDES FEMMES, LA PATRIE RECONNAISSANTE, To The Great Women, the Grateful Homeland. It was riffing on the building’s original 1790 gilt inscription, AUX GRANDES HOMMES… and advertising the current exhibition with portraits of Simone de Beauvoir and other women in French history. I sat there alone in the sun overcome with gratitude. It was 2008. I would soon turn twenty-seven and I had taken myself to Paris for the winter. The women on that banner felt like my ancestral benefactors for this feat of modern day independence. And I thought to myself, If I can pull this off, what can’t I do?
MY THIRTIETH BIRTHDAY APPROACHED. MY novel was finished, but no agents were interested. The time felt right to abandon my pursuit of never growing up. Sure, I could have stayed in Key West, continued toiling away on the boats, trying to write another book that might also never get published, but that felt like a dead end. I decided to shift gears and try my hand at writing for newspapers and magazines. I set my sights north, one hundred fifty miles up the Overseas Highway to the nearest city.
Miami came into focus as the perfect blend of what I loved most about Key West and New York. It had the sun and the sand, but it was also a cosmopolitan, international city. And so, at the end of Key West’s annual Fantasy Fest bacchanal in late October, I packed up all of my earthly possessions in a few cardboard boxes and made the drive north with my new Pomeranian puppy, Rascal.
When I arrived to my oceanfront condo on South Beach, I stepped onto my balcony alone and gazed beyond the pool deck to the aquamarine ocean as kiteboarders whipped across the waves. Inside, the apartment was empty. I’d need to build a life here from the ground up. Daunted by the enormity of that task, I said to myself as a way of self-soothing, “How can you ever be sad or lonely when this is your view?” And for the most part, I was right. I lived in that apartment for the entirety of my near decade in Miami. Every morning I awoke to that view felt like a miracle.
Miami is where my love of travel and my passion for writing coalesced into a career. My first big break came from the Miami Herald where I became the inaugural hotels editor at Miami.com, the paper’s lifestyle and entertainment website. I was now a part of a team of smart, savvy, dynamic (mostly) women who reported on the city’s restaurant, nightlife, fashion and arts scenes at a time when Miami was in the midst of rapid growth and development, a trajectory it’s still on today.
I grew up in a household where the newspaper was on the kitchen table every morning, so I took pride in seeing my byline at the top of stories with weekend road trip itineraries, summer travel ideas and celebrity chef profiles. I also found it incredible that I was publishing stories alongside legends like Carl Hiaasen, while my friends and colleagues were winning Pulitzer Prizes for investigative reporting. As my career evolved, I eventually wrote feature cover stories for nearly every section of the newspaper and its lifestyle magazine.
Soon, I was introduced to an editor at The Telegraph in London where I became the Miami destination expert, checking into and reviewing nearly every hotel in South Florida and writing comprehensive travel guides. I traveled extensively throughout the Caribbean, Central America and South America, publishing stories in national magazines, including Conde Nast Traveler, Nat Geo Traveler, AFAR, American Way, BOAT International, Maxim, Time Out and Forbes. It was an exciting time in life, jet setting on assignment, attending hotel openings, interviewing celebrities and covering big annual events, like Art Basel.
Still, even as I moved to Miami, I had an exit plan. I thought of it as a testing grounds for my writing career. If it went well, if I could hack it, if it was really something I wanted to do, I would give myself permission to pursue a master’s of fine arts, ideally back in New York City. But Miami turned out to be much more than a stepping stone along the way. It’s a city that embraced me; a place where everyone felt like a slightly mixed up new arrival, so I fit in just fine. My friends from Latin America came as babies or teenagers, the Jewish diaspora intersected with the Cuban diaspora, my friends from the Northeast arrived as college students. And I showed up by way of Key West and also my unanchored childhood. Together, we coalesce into a deeply idiosyncratic culture that is uniquely Miami. It’s a place where I found success, deep and abiding friendships and community—a word and a concept that always irked me because it felt so elusive; until all of a sudden, miraculously, I realized I was a part of one.
I’ve been back in New York for almost six years now, but I still consider Miami home. It’s an extension of Key West, my psychic hometown, and the place where a girl, who never really wanted to, could actually grow up.
THERE IS NOTHING EASY ABOUT living in New York City. Add a global pandemic to the mix the moment you finish your MFA at Sarah Lawrence College, forcing you to hunker down in Greenpoint (which I came to refer to as the rural woods of Northern Brooklyn) and it’s downright bleak. But that’s the situation I found myself in. What is New York if not a struggle? Four years later, I sometimes feel like I’m still just starting to live the life I set out to here.
I found my way back to Manhattan, to the Upper West Side, my first neighborhood in this city where I first struggled twenty years ago—although, I live twenty blocks south now in the heart of the neighborhood as opposed to on its fringes. (“One block for every year,” as my father once put it, “you’ve come a long way.”) My apartment has an enormous south-facing window that frames a tree in the foreground, whose leaves I watch change with the seasons, and a city skyline view layered with brick facades, water towers and a single skyscraper piercing the horizon. It feels like a theatrical backdrop of Manhattan—and elicits nearly the same thrill as my ocean view in South Beach. On the weekends, in the mornings when I awake, the helicopters that buzz over Central Park sound like jet skis to my ears, so I can pretend for a few moments that I’m still slumbering by the sea when in reality, it’s the Hudson River, once again, that’s just a few blocks from my window.
When I lived in Brooklyn, getting reacquainted with the city on my early rambles, I found myself, time and again, in or near Central Park as if pulled by a magnet, sometimes with the feeling of coming-to and wondering how I got there. It’s the same way I’m pulled towards the docks in Key West or to Notre-Dame in Paris or the ocean at the northern edge of South Beach. There’s a gravitational pull in each of these places that feels like home because they were home. That’s how uptown Manhattan feels to me and I take comfort here, just as I did twenty years ago, in a jog around the reservoir, where the whole city seems to wrap around the park in a fisheye lens, a stroll down Broadway in search of a luxurious pedicure or a crosstown bus ride en route to Bloomingdales, which I’ve always thought of as the Tiffany’s to my Holly Golightly, a surefire curative for “mean reds” or city blues, achieved simply by browsing the beautiful merchandise.
My writing journey continues here, ever a delicate balance between my professional and creative pursuits, where I sit down every morning and write with Rascal nuzzled at my hip in the same upholstered dining room chair and draftsman-style desk that I bought to fill my empty South Beach apartment. My byline has found its way into new publications. I’ve published essays and a short play in literary magazines, and that short play has also been selected for staged readings with small theater companies in the city. This reengagement with drama is a return to the art form that I first fell in love with and it also feels brand new. I’m currently working on my first full-length play and I’m hopeful that it’s the right vessel for the story I’ve been trying to tell after all these years.
For the first time in a long time—maybe the first time ever—I have no grand scheme about my next move. While it took uprooting myself from Miami—a place that, perhaps only in hindsight, I realized had become home—my move back to New York sprang from the same desire to find a place to anchor myself with endless potential for growth and inspiration. I don’t know if I’m cut out for New York for the long haul. (I’m not sure I even know what a long haul is.) But, for right now, I can think of no place on earth more exhilarating to continue to chip away at the incremental stuff of life and pursue my art.
HOTELIGENCE HAS BEEN A WORK in progress for the last six years. The idea first sparked after a conversation with one of my editors at the Herald shortly before moving back to New York. I’ve spent the last year building the site in earnest. Hotels became my calling card in Miami, my area of expertise and also a passion. Where I lay my head at night has always been the linchpin in my travel planning “because where you stay is your first impression of any destination,” the Hoteligence tagline. This was one of my earliest travel epiphanies, gleaned from bouncing around Europe for the first time, in and out of hostels and pensiones, in France and Italy as a college student after studying abroad in London. That was also my first taste of the freedom of solo travel, departing from my friends in Nice to spend a few days exploring Florence, Venice and Rome on my own before reuniting in Lake Como. In those instances, securing a safe, comfortable place to spend the night was paramount.
Travel is an act of courage. To plunge yourself into a foreign place—whether it’s the next city over or halfway around the world—requires energy, adrenaline, a willingness to be out of your depths. It’s a test of your adaptive, improvisational and, ultimately, survival skills. Travel can be thrilling, it can be draining, it can be frightening, it can be awe-inspiring; it’s rarely dull. The relief that comes in closing your hotel room door to all that’s unknown in the outside world is a return to the self, a place where you can just be. In my travels, the cosseted respite of a hotel room is both essential and profound. Luxury starts with privacy and then knows no end. Pico Iyer once said, “All you need to travel is wonder and a Swiss Army knife.” I tend to agree. And I suppose my Swiss Army knife—or at least one of its sharpest blades—is the perfect hotel.
I want Hoteligence to be as useful a tool as that Swiss Army knife in your travel planning. That’s why hotel reviews are at the heart of the site. In the weeks and months to come, I will be migrating over 200 reviews onto Hoteligence, spanning North America, Europe, the Caribbean, Central America and South America. Beyond the practicality of the Swiss Army knife and the perfect hotel, I also want to capture the wonders of travel. After all, it’s the moment after you check into your room that the real adventure begins. Our Travel Stories column is home to practical guides, dispatches and stories, while Letters & Leisure is a place for long and short form essays, humor, criticism, experiments and other musings.
You may notice that New York, Miami, Key West, Paris and Southern California are strongly represented on Hoteligence. After all, these are my “soul cities,” the places I return to over and over again because, to the little girl inside me who never really knew the comforts of a hometown, they feel like home. But you’ll also find plenty of other destinations, many with the same spirit. I’m obsessed with islands and global beach and maritime culture, whether that’s a surf break in Costa Rica immortalized in a classic surf film or the rock formations in the Mediterranean off the coast of Ibiza where Odysseus was nearly shipwrecked by sirens. I love big cultural capitals where, by simply wandering the streets, a portal opens into a place’s history, architecture, arts, food and fashion.
As Hoteligence grows, I look forward to welcoming contributors and expanding our destination coverage. (If you’re a traveler and/or writer interested in contributing, just shoot us an email at hoteligencelife@gmail.com and say hi!)
While so much of my itinerant life has been a subconscious search for home, I also travel for escape, adventure and pure pleasure. The tension between my desire to shove off on my next adventure and also throw down an anchor that catches has emerged as the enduring paradox of my life. Through the years, though, I’ve come to realize that the fish out of water feeling I first experienced as a little girl in Nashville is actually the state where I feel most alive. It’s in those moments of discombobulation when I’m actually the most tuned in, the most observant, the most curious, the most open to wonder and exultation. For me, solving the mystery of a place I’ve never been before is an inquiry into how it fits into the geographic and historic puzzle of our shared humanity. “Why do you talk like that? Do you know how to say YOU ALL?”
I’m excited for the road ahead. Thank you for coming along for the ride. It’s going to be a good time.
Judy Benowitz
I love your back story. So beautifully written.
Love mom