For the tourists who buy conch shells in the crushed-coral lot of the Southernmost Hotel, where U.S. 1 runs out of land after its 2,000-mile descent of the eastern seaboard, Key West is a party town–the end of the road in the sense that senior prom is the end of high school. It is a place where letting go begins with a beer in the Half Shell Raw Bar, pauses to take in the sunset at Mallory Square, then finds its stride in a neon careen down Duval Street to Sloppy Joe’s, where Hemingway told tales and hitched his pants with anchor rope. Anything might happen from here on out. Something surely will.

For others, Key West is the end of the road in the way that the darkest bar is the end of the day. It is where shattered lives exhaust their final hours, where fortune-tellers manufacture hope for the hopeless for a $10 bill, where men who can’t recall when it all went wrong lean in 2 a.m. shadows among six-toed cats that are scarcely more than shadows themselves.

In Key West, people who would pause to consider if they were farther up U.S. 1, or farther up the ladder, don’t. And those who don’t smoke might just light one up.

At 5 a.m. the town is at slack tide. The shutters are drawn. The only sound is the grind of the tires as Mo and I pedal our rented bicycles up White Street. A liquid trail of Spanish beckons us toward the deli at the M&M Laundry, where we stop for Cuban sandwiches to go and shots of sweetened espresso. A feral rooster named Ernesto, his broken feathers trailing through the dust, pecks up scraps behind the kitchen.

“If you need sandwiches tomorrow morning, try the Ernesto,” the man behind the counter tells us. He jabs with his chin toward the rooster and smiles under a stained mustache. “It will be tough, but good.”

“Mañana,” I reply, but unless a storm shuts the airport down, there will be no tomorrow for us. This is our last day fishing the flats, and if our luck continues to hold–and it has now for 10 years–once more we will go home having failed to reach the goal that brings us back. For if Key West marks the end of the road for the young in spirit and the heaviest of heart, it is also the last stop for the intrepid angler who can’t rest until he has taken all the world’s great gamefish. After most fishermen have boated their first tarpon, after the bonefish has made its last run and the Atlantic salmon is hand-tailed in the gloaming of the castle ruins, the permit dangles just out of reach, flashing its mirrored sides like a tropical jewel.

Growing up to 70 pounds, permit are the largest member of the pompano family and the only one that’s more famous at the end of the line than on a dinner plate. They sport large eyes and cavernous nostrils, so that what they don’t spot as a phony, they sense as a counterfeit. Not that many of them stick around long enough to inspect your offering. Permit typically spook from the boat at 100 feet, or else they scurry away the moment you lift the rod.

Mo and I have commandeered the services of Simon Becker, one of the best permit guides in the Keys. He is already at the dock by the time we’ve locked our bikes at Garrison Bight, a good-morning smile on his lips and two fists full of fly rods. It takes just a minute to slip the rods into the racks on his skiff and put the sandwiches on ice. Then we are idling off past the sign for the Harbor Lights Restaurant–Entertainment, Romance and Live Bait. In another minute the boat is on plane, shearing the rippled moonstone surface.

We’re reserving the first two hours for tarpon, until the sun is high enough for us to be able to spot permit on the flats. Simon cuts the motor inside a necklace of mangrove islands, and I step up on the bow with the 11-weight, feeling the way a fighter must feel when he dances into the ring to face a better man. Tarpon fishing is the most masochistic experience I’ve had holding a rod, not because tarpon are difficult to catch but because after the first few jumps it’s just your muscles against theirs, and then after a half hour or so it’s your heart against theirs and a sober question as to whose will give out first. Men pay $500 a day for the pleasure.

Two hundred feet away a reptilian back arches out of the water as a tarpon gulps air, its scales reflecting the fire of the sunrise. The line pulses out and the fly falls, is pulled once…and stops. I will spare you the details. Suffice it to say there is a point early on when we are looking up at 6 feet of fish coming down, and another, seemingly moments later, when the fish is so far away that, jumping, it looks like a tangerine minnow imprinted against the mangroves. The battle is won, technically, a half hour later and a half mile away, when the leader comes back to the rod tip. But no one has told the tarpon. It wrenches its chromium-plated head and spits the fly.

I sit back, exhausted, as Simon examines the frayed shock tippet.

“That looked like more fun than eatin’ ham,” Mo says. But he makes no move to take the rod. He is nursing a sore back and wants no part of the brutes this morning. I work my cramped fingers and step back onto the casting platform for round two.

Mercifully, the next hour produces no tarpon. When the sun reaches a 40-degree angle, Simon pulls up a flesh-colored mask to protect his alabaster complexion and steps down from the poling platform. He flips open a page of his tide book and cocks his head an inch, which is about as expressive as he gets when making a decision.

“Permit tide?” Mo asks.

“Permit tide.” Simon snaps the book shut and we are back on plane, heading for the unspoiled backcountry of the Marquesas Islands, 25 miles west.

The skiff slices panels of exquisite color: tan olive flats bisected by a jade ribbon, aqua­marine shoals bordering a belt of sand bottom that seems lit from within, a brilliant swatch of royal blue, the India ink depths of the Gulf. A picket line of cormorants perched on the ribs of a shipwrecked skeleton rise in an ungainly flapping. Mo points to them, but I am drifting away, reeling back through the years to a time I worked in Islamorada, farther up the chain of the Keys, where I first felt the pull of permit.

That year I had managed to guide myself to both bonefish and tarpon with the aid of a johnboat and a 20-horse Evinrude that you could trust to get you somewhere, but not to bring you back. Permit were well beyond my reach, or at least I thought so until a charter-boat captain drew me a map in the Tiki Bar with fingers as blunt as robusto cigars. He belonged to that class of citizens whose minds seem to go far away after each tilt of the bottle, so far that you have to tap them on the shoulder to bring them back. “Oh, sure,” he said. “Left at the sign that says Eggs.” I scribbled some more and walked to the bayfront shack I rented with the hope that if the right tide coincided with last light, X marked the spot where I might wade within reach of a tailing permit.

The directions were to a nude beach near Marathon, a fact the captain had failed to mention. A half dozen folks with skin tones ranging from newly minted to very old penny were grouped around what looked to be a water­logged bale of hay, and which in fact was what in the drug trade they call a square grouper, a bale of marijuana washed up after being tossed from a boat. A middle-aged woman with sea oats wound into her hair departed from the group to ask me what I was doing there–a look of skepticism coming into her eyes when I mentioned the word permit. I had to assure her I meant a fish. The nature worshippers departed at dusk, minus the grouper, and I found what I’d come for shortly after, a forked tail coaxing me to wade deeper than I had wanted, toward a dark edge where a channel cut into the flat.

It would take me two casts to hook the fish some anglers spend a lifetime and a small fortune to never catch. The backing peeled off the reel, and when the metal core showed through I clamped down and broke the permit off. It took, maybe, a minute. It left me shaking for half an hour. I drove north on U.S. 1 a few weeks later to begin a different chapter of life, during which many different kinds of fish would come to hand, but that was as close as I ever came to catching a permit.

“Mo, did I ever tell you about the time–” I begin when Simon cuts the motor.

“Yeah,” he says. “Grassy Key. You hooked a bonefish and thought it was a permit.”

“It was a permit.”

“O.K., Keith, it was a permit. I mean, you were the only one there.” He shoots Simon a wink. “Just stand back now and let me show you how it’s done.”

He takes the bow as Simon begins to pole along the outside lip of a 10-acre flat. Staghorn corals pass under the boat; turtle grass flows like gentle hair with the tide. We are looking for permit leaving the interior of the flat as the current flows out, working toward deeper water. The usual suspects–stingrays, boxfish, midget barracudas, and nurse sharks–seem to be in particular abundance. Simon takes it as a good omen.

“There’s a fish at 10 o’clock,” he says. “About 200 feet. O.K., it’s a permit. He’s at 150, do you have him?”

I have him, but then I’m standing on the cooler getting a tan. There isn’t any pressure on me. Mo is looking in the right direction. There was a time when both he and I would have been trying to decipher the hands of the clock at this juncture and Simon’s voice would have been rising: Not that left, your other left! But now Mo sees him.

“He’s at 80 feet. Start your cast.”

It’s a good cast. Mo’s fly sinks to the bottom about 4 feet in front of the fish. The permit flares on it, tilts its nose down.


The permit runs up, turns away, flashes a circle and departs, leaving a wake on the flat.

“The permit is the only fish scared of his own food,” Mo says, and passes me the rod.

In the next few hours I have two shots at permit: a cruiser that I have to lead like a fast-flying duck and that actually stops a moment to consider; and the second, a big permit potted up in a small depression of the flat. I overcast him by 3 feet, causing Simon to remind me that the fish doesn’t eat from that end.

It is midafternoon when we make our last stop in a cove on the backside of the Mar­quesas. Simon poles along a depression that worms across the flat while Mo stands on the bow, the yarn-crab fly pinched between his thumb and forefinger. The tide is almost shot, hope going with it, when Simon quietly says the magic word. This time there isn’t any frantic search to see the fish. Five permit are nose down, their forked, liquid tails out of the water, beckoning like ebony fingers.

“Don’t get nervous, Mo,” Mo says. Simon poles toward the fish, cutting the distance to 100 feet. A pod of tailing permit are considered to be the best prospect for a hookup, and the tension on the boat becomes palpable.

“When you’re ready,” Simon says.

A permit darts from the pack, picks the fly off the bottom, and drops it. Mo pulls the fly a foot. The water shivers as the fish jockeys for position. He pulls again. “Got him.”

A transparent sheet of water jumps up the fly line as the permit powers toward deeper water. Simon poles after it and the fight is engaged, slugged out in a channel after several unstoppable runs, and then almost lost when a lemon shark lit up by the vibrations of the permit homes in. Simon pounds on the water with his pushpole and the shark disappears. Mo, standing braced and bowlegged on the bow, turns and smiles grimly, his forehead popping with sweat.

Tiring finally, the permit begins to circle the boat, each revolution drawing it nearer. Several times it comes to the surface, then vibrates down, flashing like a coin sinking to the bottom of a wishing well. Fishing the camera out of my gear bag, I am torn between feeling quite wonderful for my oldest friend and feeling insanely, unforgivably jealous.

“How about that,” I manage when Simon’s hand shoots down into the water, then lifts with the permit gripped by the wrist of its tail.

“Smile,” I say, as if there is a need.

The photograph I took that day is fading now, and in the years since I snapped it, the face of Key West has changed with the influx of money. Fewer people come here for their last drink now, more for the first of many. The 2 a.m. shadows are no longer populated by the hopeless, and you don’t see as many paw prints of six-toed cats. Today, you are more likely to encounter iguanas on your bicycle ride to the docks than feral roosters.

But the shoals surrounding the island are there, if ever changing, and the stools we sat on in the Half Shell Raw Bar, where Mo pulled the photograph out of his shirt pocket and stared at it for about the 20th time that night, are still being warmed by those who are drawn to the end of the road. We’d had the film roll developed at the one-hour lab, and the best photo showed the slab-sided, nearly circular fish imprinted against Mo’s chest. No one he’d shown the picture to knew what kind of fish it was or seemed to care. The Key West they came to find was pretty much reflected in its entirety by the bottles behind the bar.

“Are you going to kiss it again?” I asked.

Mo put the picture back into his pocket. “This is on me,” he said, and scattered bills onto the bar.

Back at the hotel, I walked out onto the dock. A few blocks away, tourists were watching the sunset behind Mallory Square, clutching margaritas, throwing money to the talking parrots. At the end of the dock, a man leaned on the wooden rail. He tapped ash from his cigarette and considered the ocean below him.

It occurred to me then, as it does now, that in no other place I have fished has fishing been so far beside the point. But then fishermen are by nature set apart, and my end of the road is beyond the bars on Duval, beyond the glow of the cigarette on the dock. It is out there under the stain of the sunset, maybe close, maybe far, still swimming through the darkness. A part of me wishes I had caught it that day, and a part of me hopes I never will.

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