Family vacations can be trying. They consistently seem to involve an unpredictable blend of the best and worst of times, and I’ve found that maximizing the best while minimizing the worst does not come naturally.

What with three young and highly energetic boys, my wife and I learned early that an extended holiday vacation spent entirely at home could be a trying experience. Youthful attention spans are short, and a young boy’s threshold for boredom can be set alarmingly low. Sometimes a change of scenery is required. 

For us, long holiday weekends were a snap. Living a few hours from the Florida panhandle’s best beaches, we’d simply pile in the car and head eastward. The beach resort where we habitually stayed made it easy, providing rapid access to recreational diversions sufficient to keep everyone more or less content and at peace. Days were spent constructing a multitude of sandcastles doomed by the incoming tide, and nights involved a lot of take-out pizza and cruising Blockbuster for movies that would pass muster with mom. 

Spring break presented a greater challenge. Too long to remain homebound but too early for the local beaches, at times spring break seemed to us a sadistic punishment imposed by the public school system for crimes unspecified. So one year we decided to spend spring break away from home and on vacation.

As per protocol, my wife and I waited until the very last minute to arrive at this momentous decision. Raised in the Sunbelt, our two older boys were eager for snow, and we considered various destinations involving ski resorts. Not much was available at that point, however, and we consequently reversed field and shifted our focus from winter sports and wood burning stoves to beaches, sun bathing and warm, salty water.  Within a remarkably short time we were winging our way to Miami and driving eastward on Card Sound Road to Key Largo. Final destination: Key West. 

I’d been to Key West several times before, albeit never as a father with young children in tow. My experience had been positive. If New Orleans is the most European of American cities, Key West is a yet more subtropical anomaly, culturally and geographically detached from the rest of the country. I’d liked the eclectic and eccentric native population, the fact that dogs were welcome just about anywhere, the surrounding ocean and even the innumerable chickens scratching in the dirt. Adding to its appeal, Key West and Ernest Hemingway are inextricably linked, and Hemingway, both the author and the man, long have intrigued me. 

When I was ten, I happened upon Farewell to Arms and thrilled to the book’s terse prose: “In the springtime we went to war.” I found compelling the emotional restraint of its protagonist; left alone with his lover’s corpse after her death by labor, Lieutenant Henry tells us: ”But it wasn’t any good. It was like saying goodbye to statue. After a while I went out…and walked back to the hotel in the rain.”. I read the book over and over. 

But what of Hemingway and Key West? Anxious to leave Paris and based largely on the recommendation of his friend, John Dos Passos, he and his new wife, Pauline Pfeiffer, chose Key West as  their new home. The dilapidated village that greeted them in 1928 bore only a passing resemblance to the crowded island city of today. Its population, a mélange of Cubans, Afro-Americans and white American “conchs”, had diminished from 26,000 to 10,000 over the years following World War I. Its once thriving cigar industry was moribund, and most of its workers made their living from the sea. The Cuban influence was strong; fully half the natives referred to their home as Cayo Hueso.

In To Have and Have Not, Hemingway’s only American-based novel, the author described the village’s “…unpaved alleys, with their double rows of houses; the open-doored, lighted Cuban bolito houses, shacks whose only romance was their names, , , …the brightly lit main street with the three drug stores, the music store, the five Jew stores, three pool rooms, two barbershops, five beer joints, three ice cream parlors, the five poor and one good restaurant…the street that led to jungle town, the big unpainted front house with lights and girls in the doorway…”. He established a circle of friends amongst the locals, learned how to fish the Gulf Stream and drank in his favorite bars. In 1930 he made Key West his permanent address, and in 1931 Pauline’s uncle purchased for them a white stone house on Whitehead Street.

This period of relative domestication was to be short-lived. Five years later in Sloppy Joe’s, the Key West bar Hemingway made famous, he met and immediately began to woo a young writer, Martha Gellhorn. In 1940 she would become his next  and penultimate wife.

We flew into Miami, rented a car and began the drive south. For the first 60 miles or so the older boys clearly were excited and peppered me with questions (“Which key is this?”  “What’s the next key?”  “When do we get to the long bridge?”), but as darkness fell their enthusiasm waned, and my soliloquies extolling the Keys’ natural beauty provoked only a single question, much repeated: How much longer? Finally we arrived.

I’d heard of Casa Marina and vaguely recalled its location and appearance. First opening to the public on New Year’s Eve 1920, the Casa Marina was built by a railroad tycoon, Henry Flagler, as a luxury hotel intended to suction up wealthy tourists disgorged at the terminus of his key-hopping southern line. The hotel subsequently had served as a military hospital and then a federal office building before returning to its original purpose. Downtrodden by decades of tropical storms, hurricanes and the more mundane exigencies of the passing seasons, it was renovated in 2000. From the outside the gleaming white edifice continued to resemble an exceptionally well-kept governmental office building. 

Our suite was on the ground floor facing the ocean and blessedly featured a bedroom that locked from the inside and was thus securely separate from the communal living area, where all the boys (theoretically) would sleep on a foldout sofa. Our balcony looked out on the hotel’s small beach, a luxury on an island where over the years coastal development has served to divert many of the currents which for centuries before man’s arrival had faithfully provided replenishing sand. The pool and adjacent bar were quite fine, and the restaurant served breakfast al fresco in the morning sunshine, an arrangement greatly appreciated by the parents of three young boys biologically incapable of remaining seated at mealtime. 

So what does one do with young children on a family vacation in Key West, long renowned as a raunchy off-shore paradise and favored destination for gays eager to savor its sun-soaked pleasures in a libertine atmosphere free of disapproving stares? First, as with previous family campaigns involving Montana, Manhattan, San Diego and various less ambitious destinations (eg, the De Soto Caverns of Childersburg, Alabama), I first had to disabuse myself of the notion that the reality of our experience would bear anything more than a passing resemblance to the itinerary my wife and I would have pursued had the vacation been kid-free.  

Ernie was the first to go. The older boys firmly vetoed any pilgrimage to the Hemingway home, and in a quid pro quo I politely refused their pleas that we expend our time and money upon the cluster of tourist traps that have sprung up just north of Mallory Square (“Authentic Pirate Adventure!”, Ripley’s “Believe It or Not” museum, etc). 

Next was the nautical expedition. For reasons unclear to me but possibly related either to my wife’s sharkphobia or my Alabamian family’s inability to tolerate any water temperature below that of a very warm bath, my envisioned boat rental and snorkeling trip to an uninhabited cay never materialized. 

Our lunch at Sibouney, one of my favorite Cuban restaurants, was a decided flop. Wiley reverted to the simian behavior that restaurants typically inspired in him, and the older boys, their palates honed by a diet ranging narrowly from hamburgers to chicken tenders, loudly and repeatedly expressed their disdain for Cuban cuisine (“This smells funny!”). 

That meal was, I suppose, the trip’s nadir. Having at last lost patience with my beloved family’s inability to appreciate what I perceived to be the most compelling attractions of Key West, I gathered Wiley up in my arms, strode through the crowded restaurant and exited to sit on a bench and stare stonily at the passing pedestrian traffic.  After a few minutes Diane came out to sit beside me, administered a few minutes of spousal psychotherapy, suggested specifically that I perhaps consider a slight adjustment of my expectations and invited me to return to the table inside. I did, and from that point on all was fine

So what did we do with our time in Key West?  First, it helped immensely that the weather was cooperative. March in Key West can be rainy and rather cold, a circumstance deadly to parents with young ones cooped up in a hotel room with a limited supply of in-room movies and video games. Thankfully we were blessed with sunshine and warm temperatures that lent well to our wardrobe of shorts, t-shirts and bathing suits.

We all took the Conch Train, an open air faux trolley that winds up and down the streets of the city, its driver providing nonstop cheerful commentary regarding the island’s history and sites along our route. The older boys grumbled a bit at the outset but soon relaxed and remained quiet throughout the tour. From their comments and questions over the next few days, it was obvious they’d absorbed much of the driver’s monologue.  

With Wiley perched regally in a carrier seat immediately behind me, we rented bikes and explored the island. We toured a carefully restored ship that during World War II had guarded the convoys passing through the submarine-invested waters of the North Atlantic.  We rode to a public park and ambled up, over and around a fort manned by Union troops during the Civil War.  We visited Mallory Square at sunset and watched the buskers ride unicycles, juggle machetes and put performing cats through their paces.  

Every day we spent hours on the hotel’s beach, Diane sunbathing and blissfully insulated by her i-pod, me building elaborate sand castles with the boys.  When left to themselves, the older boys spent much of their time attempting to knock coconuts off the palms and imploring the city’s street crew to assist them in their efforts. This resulted in our accumulating approximately 700 lbs of coconuts, only a fraction of which made it into the suitcases for the trip home.  

Some evenings we strolled down Duval, Diane vainly attempting to distract the obviously fascinated older boys from the more pornographic t-shirts on display in storefront windows, and bought the usual trinkets and knick-knacks. When our week was up, we arose early for the drive back to Miami and the flight home.  

Most of all we simply enjoyed being together, and while the exotic, subtropical environment, beach, ocean and fine weather certainly helped, I think, or at least I like to think, that sharing the challenges and rewards posed by travel strengthened us as a family. That to thrive even absent the familiar trappings of home reinforced in us the certainty that we could depend on one another. Over the years since that experience has been duplicated on more ambitious expeditions to Mexico, Costa Rica, Spain, South Africa and Paris.

As we flew homeward from Miami, I glanced over at my wife and then down at the stack of papers on my tray table, excerpts from the manuscript of a book I’d long been writing.  I recalled Hemingway’s first wife, Hadley, and how in the winter of 1922, while traveling from their home in Paris to join Ernest for a skiing holiday in Switzerland, she lost on the train a valise containing the only copies of his works-in-progress. 

She’d been frantic with remorse and Hemingway characteristically dark in response. To others he later would attribute the subsequent dissolution of their marriage to the lost valise. It’s likely that no one ever will know the true contents of that small suitcase, but no matter what it contained, the paths to nowhere so familiar to all writers or the seeds of a great novel, to me his attempt to pin the source of their marital failure on this, his wife’s now-infamous misstep, rings hollow. His marriage to Hadley, his need for Hadley, had run its course.  His immediate future lay in Key West with Pauline, the wife soon to follow.

Therein, perhaps, lies some evidence of the tragedy inherent in Hemingway the man, of the emptiness that co-existed cheek to cheek with the greatness. In his letter of acceptance after receiving the Nobel Prize for literature in 1954 he wrote, “Writing, at its best, is a lonely life…For [the writer] does his work alone, and if he is a good enough writer he must face eternity, or the lack of it, each day”. 

This is, at once, the most accurate, moving and bleak description I’ve ever read of what it means to be a writer, and the words eloquently bespeak Hemingway’s ever-increasing despair. As his biographer, Carlos Baker, put it, he was haunted by the “nightmare of nothingness”. No new locale, no matter how exotic; no number of marlin taken from the Stream nor braces of duck shot from the blue Idaho skies; and no new wife, however idealized, was sufficient to assuage for long the inevitable loneliness or to fill that “empty spot” to which he so often referred. And as age, his prodigious drinking, a series of head injuries and his increasingly effortful attempt to maintain the virile image his public had come to demand removed from him his ability to write, there was no more filling that emptiness. Even as a young man he seemed to anticipate the end awaiting him; as he wrote in Farewell to Arms: “The world breaks every one…those that will not break it kills.”

Since my initial introduction to Hemingway I’ve read most of his published works, a number of his letters and at least a dozen biographies. Over the years, both by my reading and by visiting many of the places of which he wrote, I’ve attempted to trace the path of Hemingway’s tragic odyssey.

I’ve roamed the Basque country he glorified in The Sun Also Rises and lingered in the old Shakespeare and Company bookshop on the Left Bank of the Seine. I’ve toured the first home he owned, the lovely old house in Key West. Not far from his last, in Ketchum, I’ve stood in the icy waters of the Big Wood River and cast for trout, the treeless sere mounds (“hills like…elephants”) of Camas County rising gently to the west. As the golden leaves fell around me, I read the inscription on the simple memorial that stands unobtrusively beside the road that runs past the Sun Valley Lodge ("Best of all he loved the fall…”).  

I’ve scarcely been alone in this endeavor. Untold hordes of writers, would-be-writers and simple aficionados have done the same, and each presumably has reached his or her own conclusion as to what forces eventually drove this man to self-annihilation. Whatever the conclusion, in tracing his path one finds evidence at every step at of a man who acknowledged his personal demons, confronted those demons as best he could and in the end finally lost the capacity to resist them. From the cacophony of emotions and experiences that comprise a loving family one may achieve equipoise, but to this great and sad man whose work has provided such pleasure to so many was denied the surcease of even this homely remedy. 

Catching my glance, Diane leaned into me and brought her lips close to my ear.  “We’ll go away like this every spring break,” she whispered.

The plane banked slightly, pressing her more closely against me. “Yes,” I said. “Isn’t it pretty to think so.”

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