Big brown pelicans in Islamorada, Florida Keys

Taylor Hagood: Key West Dreaming

When I received my Ph.D. in a year I shall not name, a friend of mine gave me a book written by Joy Williams entitled The Florida Keys: A History and Guide. I was about to move to Florida to start a job as a professor, and I had little concept of the Keys. The only thing I knew about the place was that there was a store in Key West named Fast Buck Freddie’s because my family then had a refrigerator magnet manufacturing business, and Fast Buck Freddie’s carried the products. Fast Buck Freddie’s: I love writing that. It seems to me that if South Florida should ever become a nation of its own it could be called Fast Buck Freddie’s.

But back to Williams’s book, as I looked at the cover, with its blue sky and palm fronds with a beach peeking through, I had no idea how deeply my life would take root in Florida. I remember moving down, my father driving a U-Haul while I drove my red Nissan pickup truck (that as I now write has over 400,000 miles on it and which I really must make myself get rid of. Do not worry, I have a newer vehicle, too, just in case the Nissan acts up). We stopped at an antique store at Micanopy, and I remember the lizards scattering in front of us as we walked in.

Whooee! — I was on my way to a job in Jurassic Park.

The book stayed in my mind as I moved in and started my job. Those were some high times, let me tell you, or at least they were in my mind. After the well-below-the-poverty-line income of a graduate teaching stipend, I felt pretty sure I had all the money in the world. I went out and bought my mother a nice bracelet. Then I bought myself a convertible. Went to the beach pretty much every day. Got myself into a relationship with a beautiful lady. I mean . . . .

That Drive, That Water

I did not get down to the Keys until May, just after my first academic year ended. I experienced mixed impressions in the early phases of the journey. I started with real excitement as I drove along Highway 1, where the cement divider painted pale blue streaks through the still Everglades. The little bridge over Jewfish Creek showed me the beginning of the islands. Key Largo—well, it seemed not so great, really. But then the land started to give way to that water. I have tried so often to find the right word for its color: blonde? teal? Crest-toothpaste blue-green-white? None of those quite get it. Maybe it is best described by its effect, which for me amounts to a precipitous drop in blood pressure and a feeling of never wanting to leave.

I have made a few drives on some of the great roads. I well remember riding on that harrowing cliff-hanging path along the Amalfi coast, the sheer drop to the Mediterranean below, buses honking as they edge by each other on the sharp curves while Vespas zip between them like wasps defying elephants. I recall a lambent drive up the Natchez Trace by moonlight, and I will never forget literally coming around the mountain to a first glimpse of Yosemite Falls. But nothing for me can match the road from Florida City to Key West, and when I drive it now,I get the same feeling I did the first time.

The route that builds to a crescendo like a Bobby Darin song. Through Key Largo and the dreamily-named Islamorada, that water teases more and more, glittering and dancing. You hit Marathon, where for a moment you feel disappointed that here exists regular old life, even if it does have an island whiff about it. But then you start over Seven Mile Bridge that stretches along beside the old railroad bridge—that forlorn yet indomitable monument to Henry Flagler’s century ago “folly” —and you know you have hit the crescendo. The rest of the way literally grows more awash in that delicious blue-green-pale water, with now only clumps of mangroves after you pass Big Pine and Cudjoe.

And then . . . .

Key West

Am I really here? I thought that day. Can this place be so real-not-real?

From the moment I moved to south Florida I felt very sensible of being far out in the water, away from the mainland. When I got to Key West, I felt very sensible that I had left United States civilization behind altogether.

At first I passed recognizable chain stores and hotels, but once I got into the old town, with those wonderful wooden houses, and took my first stroll down Duval Street and got a glimpse of some of the wares in the stores, I knew I really had left the country behind.

Of course one of those stores was Fast Buck Freddie’s, and it was a strange experience to go into that exotic store in this exotic place and see the magnets my family made.


Let me talk history. When the Spanish arrived—led by old Ponce de León himself—they called this place Cayo Oueso, meaning “Island of Bones.” It seems that human bones were strewn about, apparently the work of the enigmatic Calusa Indians who lived here. The name, Cayo Oueso, of course, sounds somewhat like “Key West,” although that designation seems to have come later, either as an anglicanization or Americanization of Cayo Oueso or (or perhaps and) referring to that particular Key as westernmost of the tiny islands with fresh water sources in this area.

It is with a different, a later, Juan that the Cayo Queso story takes on energy—this was Juan Pablo Salas, an officer in the Spanish navy, who was deeded the island by the governor of Cuba in 1815. When Florida became part of the United States six years later, Salas saw an opportunity for some Yankee dollars and decided the island was so nice he could sell it twice. Sold it to a couple of johns (it is hard for me to refrain from talking about Florida land in terms of prostitution).

The first time, Salas sold it to General John Geddes in exchange for a sloop. Then he sold it to the more-often-remembered John Simonton for about $2,000 in pesos. This maneuvering naturally set up a tense bit of vying for ownership; Simonton evidently had bigger guns in Washington, D. C., who stepped in to recognize him as the official owner.


The intricacies of this purchasing can grow quickly tedious, and tedium sits uneasily in the context of Key West, so I think it better to focus on why Simonton and Geddes wanted the island. The answer lies in its unique position, which Simonton’s friend, John (!) Whitehead, explained to him based on personal experience. Key West has a deep harbor, which allows for large ships to dock there. This harbor is part of an equally deep shipping lane that connects the Atlantic Ocean and the Gulf of Mexico. What really makes the position special, however, is that this deep water is surrounded by very shallow water—that pale, sparkling expanse of rapture—which spelled high danger to ships. It was that treacherous shallow water that really made the island a great possession because it furnished its lucrative industry: wrecking.

What a business, wrecking. It is essentially a polite version of piracy. Ships would wreck on the reefs all around the island, sometimes (well, often) encouraged by the island’s inhabitants. One of the favorite tricks was the same one used at Nag’s Head in North Carolina: hanging lanterns around the necks of four-footed beasts at night to trick ships into thinking they, the lights, were those of other ships safely in a harbor that was not there. The real ships would make for the lights only to crash on the reefs. Islanders kept a watch out for ships, and when one wrecked they tore out to it on their boats, the first one to reach the wreck having first rights. Where pirates may have killed or ransomed the passengers, the island wreckers took great care to see that the crew and passengers were saved. But they made sure to take their possessions. It seems that Whitehead had been just such a victim and saw how lucrative it could be on the other side of the wrecking arrangement.

Key West – Mel Fischer Museum – July 2017

There is a story of a minister, a brother Egan, who once was preaching in a church on the island. He could see out a back window that a ship had wrecked, and he decided he wanted to be the first one out to it. The folks gathered there listening to his sermon watched him walk out of the pulpit and up the center aisle, preaching his heart out. Finally, as he got close to the back of the auditorium, he started quoting I Corinthians 9:24, “Know ye that they which run in a race run all, but one receiveth the prize? So run that ye may obtain.” And with that he himself ran, fast as he could, right out the back door and as quickly as possible to a boat to head out to the wreck and to fortune.

Wrecking is crucial to understanding the foundational atmosphere and mentality of Key West, in my view. It was an exploitative practice to be sure, and yet there is something pathetic in it. Most of the plunder was auctioned, but sometimes the people of the island would keep things for themselves. I read once about a family who kept monogrammed dishes, but the plates they ate from bore not their own family’s initials but those of whoever either already owned them or was supposed to own them. Borrowed initials, borrowed wealth, disrupted plans—these are the legacy of the Key West wreckers. There is something touching in the image, I think. People stuck off on an island happy to be a law to themselves and glad to enjoy the possessions and dreams of others.

Wealth and Growth

Wrecking brought tremendous wealth to the island—so much that the United States government thought it wise to get in on the action. The government passed the Federal Wrecking Act in 1825 for the sole purpose of issuing licenses to wreckers and establishing ports of entry, Key West being one of them, where federal warehouses were constructed, and federal auctions held. One of the authorized auctioneers, Richard Fitzpatrick, made as much as $10,000 in fees in a year (around $300,000 now). Imagine what the government made.

Other lucrative industries soon followed. Fitzpatrick is important also in another early industry on the island. This industry was salt gathering. About a decade later, in the 1840s, Bahamian immigrants built a strong sponging business, and in the late 1890s, a Greek man named A. J. Arapian became a well-known diver for natural sponges. In the late 1860s, the cigar industry took off as Cubans fled their home in the midst of conflict with Spain and opened factories in Key West. The most famous of these entrepreneurs was Vicente Ybor, who by the mid-1880s grew tired of strikes on the island and so went to the Florida mainland to build his own company town called Ybor City.

I mention all these various industries in order to share what might be a surprising fact—that by the turn of the twentieth century, Key West, stuck out there on a tiny 4.2 square mile island cut off from the mainland, was actually the largest and wealthiest city in the state of Florida.

When Flagler’s ‘Overseas Railroad’ and accompanying hotel arrived in 1912, tourism became the leading driver of commerce. His primary motivation for doing the nearly impossible was the imminent opening of the Panama Canal and its promised boon to regional trade. The dream ended abruptly in 1935 when a Category 5 hurricane blew through the Keys damaging large sections of the tracks beyond repair. The furious act of nature along with the dampening effects of the Great Depression put the island back into a relative slumber.

But it is a resilient little haven. Due to its strategic location, often called the Gibraltar of the West, naval bases have played an important role in bolstering both national security and the local economy. Visited often by presidents, Harry Truman made his winter home at Fort Taylor in Old Town, which is now called the Truman Annex.

Key West Now-ish

But, just as tedium deserves no place in Key West, too much focus on labor and industriousness can quickly grow tiresome. Not that commerce should be ignored, even in our own moment. I would mention one business I love—Kino Sandals, started and owned by Cuban immigrants, Roberto “Kino” Lopez and his wife, Margarita, in 1965. You must go to this place. They manufacture and sell sandals, all made right there in your view, on display. You can try them on and buy them right there at a very reasonable cost. And they last and last. I once heard a lady telling about losing one off her foot during a boat ride and finding it floating later. Twenty years thereafter the pair remained in great condition.

I would also mention a few places to eat. I am partial to the Cuban restaurant off Mallory Square called El Mason de Pepe. For breakfast, I find it hard to beat the Banana Café, a little place with a lot of panache (if I should ever live in Key West, I will have to have one of the crêpes there every day of my life). I suspect Sloppy Joe’s needs no introduction, its sandwich being very famous if still secondary to its drinks. Key West offers more in the way of famous drinking establishments than great restaurants.

Most of the commerce at this point is of the tourist variety, with souvenir shops galore, restaurants, museums, rum distilleries, trams, bicycle and moped rentals, hotels in the beautiful houses in the old part of town. This commerce tends to be a turn-off for folks who remember the city in older times, particularly now that the cruise lines have arrived; they often grumble with good reasonabout it having become ‘Disney-fied.’And certainly the legions of University of Florida and University of Georgia fraternity and sorority siblings who descend upon the city in March can seem strangely flimsy and out of place in the city. On the other hand, their appearing for a good time with a dose of naughtiness differs only in style from the bikers who appear at a different moment or the decadent crowd that sprouts in a bouquet of painted flesh for Fantasy Fest.

Naughty(cal) but Nice

We had better acknowledge Key West’s decadence and that another aspect of tourism features strip clubs, drag shows, sex shops, and even a restaurant that offers naughtily-themed chocolate concoctions. “Innocent” is a word that hardly belongs in Key West, yet there is a quality not exactly of innocence but free exuberance that drives the very heartbeat of the place. Key West folk take things easy, just as the old wreckers did. They will gladly enjoy their own stuff or that of others. Many of them want very desperately to be happy, are determined to be happy, are happy. They are far from the mainland. Far from normal and the land of normal. They live by different rules. Or no rules at all.

If there is anything even remotely like a rule it is to embrace sensuality. Resisting that sensuality can be practically futile; the place draws you in amid a slow swirl of fingers. Or not so slow—I knew another woman who went to Key West on a weekend trip and stayed two years, funding herself by working in a swimsuit store. She did not make a fortune and then move into island life. She just went, no thought of the past or the future. Key West can do that—mesmerize you into the dream that you really can leave everything, fall in love with a place and maybe a person or persons in it, and then stay and stay.


That dream of freedom lies so fully in the heart of artists, and it is no surprise that the city has drawn them. Key West features a number of galleries, many of them full of paintings and sculptures that capture the colors of that water, the old buildings of the city, the lush foliage, boats, even the chickens that bob about freely on the streets. I bought my first ever original painting there, a small watercolor by Ann Irvine entitled “Sunrise: Key West.”

The Key West artist who most gets my heart is Mario Sanchez. This man of Cuban heritage had a studio set-up outdoors, where he would produce his artworks, which were bass relief carvings that he painted. They were scenes of Key West from his memory, with stores, cigar factories, and people now long vanished. The pieces themselves bear a vibrant, homey beauty; they are pricelessfolk art. And Sanchez was an unschooled artist who produced them in a homey way. His tools I must linger on. He did not use expensive gouges made of Solingen Steel: he used those yellow-plastic flat chisels bought cheap in hardware stores. He did not use fine bristle brushes ordered from Utrecht; he used the cheap brushes for painting houses or model cars. The paints themselves were not Windsor Newtons filled with excellent pigment: he was liable to employ stain or cheap paint that children might use.

His supplies appear in quiet humility, touching me personally. When I was about nine years old, I conceived a great interest in oil painting and my grandfather decided he would buy me art supplies for my birthday. This was my father’s father, whose own dad died when he was in the eighth grade, forcing him to pick cotton and work construction, who with his childhood cut short lived in the crude hard world of men in World War II and in a working man’s career as a crane operator and Ford salesman in Tullahoma, Tennessee. This man, who stood five-eight and weighed perhaps 150 pounds but who somehow mysteriously could move two-ton boulders and had a grip that could lift me bodily in one hand, would use his nicked and muscled fingers to pick out paints and brushes at an art store. How strange all those dainty implements must have seemed to him.

I can hear his soft voice even now in my head: “Taylor, don’t squeeze out any more of the paint than you need at first. You can squeeze out more later.”

I think of him calculating the cost of that fine oil paint the way he would have the paint for the walls of a house, his mind applying the hard practicality he had been forced to at an early age. I think of him approaching the haughty face of art with a heart-breaking innocence. This man, who rarely spoke of his war experience except to mention that he had himself operated the controls to bury his best friend killed on D-Day, stood there in the art store shelling out the cash he earned into the hope of a new world for his little grandson that would ever and always be soft and beautiful.

In my mind, just such a man was Mario Sanchez. A man unconcerned with trends, who expressed out of the simple expressionof his own heart. A man who could thrive in hard sweetness amid the crazy, endearing insanity of this strange city.


The very famous artist, Winslow Homer, stayed in Key West in the 1890s, painting wonderful oils and watercolors. He understood the hues of Key West and the waters around it. One of his greatest Key West paintings, entitled “The Gulf Stream,” depicts a fisherman in a small boat surrounded by sharks. The image anticipates the greatest book inspired by Key West: The Old Man and the Sea, about an old Cuban who after a long time of catching no fish heroically hooks a great blue marlin only to see it attacked by sharks as he tries to get it home.

At this point, the author of that book, Ernest Hemingway, is practically synonymous with Key West, his house there being one of the major tourist attractions. It was actually Hemingway’s second wife, Pauline, whose Uncle bought the house (Hem was not making that much money at that point in his career, his business approach being to marry up from one wife to the next). But Papa was living high on the hog there in the island city, waking up in the mornings to write in his painstaking way to produce his few but perfect words. Then he went out fishing on his boat named the Pilar with a Cuban gentleman named Gregorio Fuentes. Then he would return home, wash up (presumably), and head down to Sloppy Joe’s to drink. This after Fuentes and he had already knocked down a great deal of rum out on the boat (despite years of that, Fuentes lived to be 105, and he would be his buddy’s inspiration for the “old man” in the novel). In the process, Hemingway wrote quite a lot, including To Have and Have Not, about rum-running between Key West and Cuba.

Ernest Hemingway House, Key West, Florida

I confess I find myself all-too-easily caught up in the romanticism of Hemingway moving about the island in the colors of the 30s. All that dark lacquered wood finish inside, the sharp green of the trees and that blindingly blue, blue, blue water outside. I often wonder how many tourists are actually Hemingway readers: the owners are clever enough to play up the six-toed cats that creep about the property, all of whom bear names of classic film stars, and I suspect many people come just to see them.

As a matter of fact, the house has a great atmosphere of peace about it; it makes one feel close to the writer. I find the writing room in the building out back especially tantalizing, humming with energy. Many folks get a kick out of the fountain in the yard that is actually a latrine from the old Sloppy Joe’s (Hemingway apparently asked the owner if he could have it since he had spent so much time with it).

My favorite Key West Hemingway story is that when German U-boats began to appear in the area, he devised a plan of coastal defense in which he would go out on the Pilar and look around, keeping a sharp eye out for the appearance of a periscope emerging out of that water. His plan was to rush over to where the periscope appeared and drop explosives into the water to destroy the German vessel.

Hemingway was not the only writer to live in Key West. Tennessee Williams actually lived there much longer than Hemingway, although Hemingway had already come and gone by then. Beginning in 1945, poet Robert Frost spent 16 consecutives winters in a cottage at 410 Caroline Street. A lesser-known but highly decorated writer who lived there was the poet Elizabeth Bishop, whose great work, “The Fish,” never loses its charm. Speaking of charm, coming-of-age author Judy Blume considered being in Key West akin to returning to her childhood. The beloved children’s book, ‘The Giving Tree,’ was authored by long-term Key West resident, Shel Silverstein. The multi-talented author also won a Grammy for writing the song, ‘A Boy Named Sue,’ recorded to great acclaim by Johnny Cash. A character as colorful as the town itself, Silverstein died of a heart attack in 1999 in his two-story, century-old wooden home at 618 William Street. The house was still owned by his estate when eerily, it was irreparably damaged by a falling Banyan tree in 2017’s Hurricane Irma.

Keys Weekly – 618 William Street after Hurricane Irma

Being There

For visitors, a Key West day must close into the suspiration of night with a visit to Mallory Square on the west end of Duval Street to watch the sunset. Here street performers gather, walking tightwires, eating flames, juggling, or just sitting and looking pretty in a mermaid outfit. The performers hustle for their pay, and they are good at their business, drawing you despite yourself.

But as the sunset accomplishes, the breeze wafting in and the sky reddening, people line the water. Boats flatten into silhouette as they drift across the view, the Gulf waters reacting in swaths and lathing rolls to the movement of the vessels, catching the colors of the sky in a pastiche of reds, oranges, and yellows. The sun dodges among purpling clouds like a toddler playing peekaboo, its smile achingly sad not to itself but to anyone reflecting on how swiftly that smile will straighten into adulthood.

Perhaps you are sitting with someone who loves you. Maybe you are surrounded by your family and friends. Maybe you are alone.

Mallory Square – July 2017 – Megan Rooney Images

You know this pageant occurs every evening, that you are visiting with thousands of other tourists, that you are no Conch (a Keys native). Maybe you imagine that sun, that water, those clouds care what you think and feel. Maybe you hope this red moment will last forever but know it will not as you watch the sun lower itself little by little until finally, a yellow sliver, it drops like a coin into a machine.

Then it is night. Special Key West night, no doubt. But night, with its old money and lust games, its faraway sleep, its creeping fears. In sleep we can be anywhere. There, borrowed or pilferedwealth, the dream of the past, the choking, often-unappreciated gift of another day,all restlike ships wrecked on the reef, their riches in trepidation, the meaning of each little thing waiting to be written, rewritten, and remembered in forgetting.

Key West Dreaming

Dreaming—whether in night or day, there Key West distills in images, sounds, smells, snitches of action. It flashes in the red gleaming swing of a machete in the sunset as a boy slices up fresh coconuts for people to drink from. It spins in the white reflector of the front wheel of a bike ridden by an old man, long-shanked, scraggly bearded, unsteady, radical in the mid-day heat and in no rush. It whispers in the mysterious and strangely barren blue line of ocean at night driving along the dark, quiet east-north-east coast by the East Martello Tower of the Civil War fort.

Key West – West Martello Tower – July 2017 – Megan Rooney Images

It wheezes with the bugs in the tall grass bent-stalked and roughly lush among the small wooden houses on Olivia Street that hold each a tiny wondrous promise. It smirks and revels in its mirrored image in the tourist who loosens up a little or a lot in a way she would never do at home and hopes her folks will never hear about. It cascades in the dramatic frozen shriek of banyan trees that drop their roots in long strings to form new trunks around grand old mansions, tree and house both proud and content and lazy, as though they have learned the secret of, hold only disdain for, and finally have settled down with full brimming confidence to ignore those ever-insistent taskmasters: respectability, time, planning, and the joke of beginning and ending.