Last updated on September 30th, 2022.

My brain hurts as I roll over in my bed in the motel on Sugarloaf Key, my first morning in Key West.

I reach for my phone, drag the back of my hand over my eyes, hoping to focus on the time, 5:45 AM. But I can only focus on the painting on the wall directly in front of me: a poor oil painting of mangroves, salt water, a flat, more mangroves, quiet, somber almost. Yes, somber. Empty beer bottles sit on the shelf of the bathroom sink, a faint reminder of last night. Beers obviously, probably a bunch. Tuna Nachos, a staple in most Key West tiki bars. A Grateful Dead cover band.

Greg and I grab a shitty black cup of coffee in a styrofoam cup, a bagel, and jump in the rental car. We were fourteen when we met – Mr. Oakes’ science class – deep in some corner of a Minneapolis suburb. We fished together for the first time about two weeks after that, and then it seems, every two weeks since then, right up until this trip to the Keys. My first, Greg’s tenth.

The first sun stretches its long pink morning arms across the highway, over the roof of our rental car, and out into the Atlantic like a sigh. My hand cuts through the breath of air outside the window as we cruise along and over the keys – filling my lungs with salt. With silver buttonwood. With warm concrete. I’ve only known the Florida Keys from popular culture: key lime pies, conch fritters, margaritas, tiki bars, flip flops, shot glasses, fridge magnets, tank tops. A literal Jimmy Buffet song personified.

I haven’t heard the song mention the concrete. But it’s here. It stretches the full length of these islands, then spiders its fingers out in small shoots from the main artery to the edge of the earth. It melts into the gulf. Into the Atlantic. It cracks and breaks into the sand. Cars drag it from their tires to small back channels and boat launches. Ours pulls into one such boat launch under four thatch palms. Two cormorants stretch their wings and argue. I can’t tell which one is winning. Maybe it doesn’t matter. The car door shuts, and they explode over the mangroves. A rooster stands on a broken plastic patio chair in the neighbour’s back yard, propped up by a cinder block, an old Yamaha four-stroke laying on it’s side. It crows, letting us know what we already know. It was once a fighter, a source of income, bragging rights. Now lonely, transient. Pecking and scratching for oyster shells.

Always the shell, never the oyster.

It’s like that in the keys. Sometimes all that’s left is enough. Maybe even more than enough. Greg and I jump out of the rental car and try to collect all our shit in both hands – coffee cups, a cold bagel with cream cheese, a six pack of beer dangling with two beers missing, a rain jacket, couple rods. I drop my bagel. The camera around my neck swings as I bend down to pick it up. We pull our buffs up on our faces and head over to greet an old pal, Nicholas, who owns a small flats skiff boat.

The water purls as we leave the mooring, and the clouds drift in front of the sun, slightly graying out the morning. The water turns gray too. It makes it almost impossible to see into the water as we blast out into the Gulf of Mexico. But the few moments during the day when the clouds part long enough for the sun to shine, the water lights up, and it becomes as clear as staring into a swimming pool. Poling across our first flat I can see it all. Lemon sharks, bonefish, redfin needlefish, little tarpon, bull sharks, nurse sharks. Lots of sharks. Rays. Barracuda. A plane of glass minnows shatters into a million pieces. A small permit races across the bow of the boat.

Nicholas, hands me a ten weight Orvis Helios and tells me to jump on the front platform of the boat. He’s direct, but kind and patient. Two bones at 2 o’clock. Thirty feet. Do you see em? I do not. Big permit, 11 o’clock, 50 feet, but I think he saw us. Hang tight. Strip some line out, get ready. Nicholas is silent on his poling platform. Watching, biting on a fingernail, thinking. Scanning the swimming pool. Quiet, but intense. Ok ok, big ‘cuda at 12. Forty feet. Literally straight out in front of you. The sun dips behind the clouds. I fire a shot at 12 o’clock, wind at my back, sailing the tube fly into the air, letting the breeze carry it an extra 10 feet, over its head. Strip strip strip! It makes a turn and runs the other direction.

That’s alright, we spooked him. That was a big cuda dude, he says with a grin. I can see his eyes smiling through his sunglasses. He swings his pole across the front of the boat over his head, over our heads, and plunges it back into the drink. We’ll get a bunch more shots, don’t worry.

Greg has always been a hunter. Elk, deer, turkey, giant brown trout, tiny spooky brook trout, big predatory musky, tarpon, permit. Anything that requires crouching, stalking, moving slowly, deliberately, physically demanding, mentally languishing at times. Hard. Catching ten rainbows in an hour on dries doesn’t really work for him. And I like that about Greg. My focus shifts when I’m around him. Senses always heighten. Intensity shifts. Today, he’s hunting permit. I’m along for the ride. I like watching, fishing a little, talking with Nicholas, drinking a few beers.

We spend a big part of the day out by the break. We can see the Marquesas Keys twenty miles away. They’re small from this distance, but we can see them. Formed by a meteorite millions of years ago, it’s the only natural atoll in the Western Hemisphere. In 1985, a Keys chicken-farmer-turned-treasure-hunter Mel Fisher discovered the shipwreck of the Nuestra Senora De Atocha, and it’s sunken treasure; silver, gold, emeralds, indigo – a $400 million score. A chicken farmer. We joke about what we would do with the $400 Million. Greg catches a cuda, I miss two. Then he catches two, and I miss one.

The day stretches on, as Greg and I trade duty on the platform, near misses, and Coronas. We also trade stories of last night, the ones we can remember. An older, weathered, drunk woman at the bar retold stories of her groupie days following Motley Crue around Los Angeles. Her deep tan leather lips gripped a Salem cigarette, and she dropped a daiquiri in her lap. We cried laughing. Nicholas broke in. Greg, tailing permit, get up there dude. Grab the permit rod. The high sun had now shifted to about two inches from the horizon. The wind died. A whisper of clouds tried to blot out the sun. Infinite shades of blue painted the backdrop. A small shaft of light broke through and I inhaled it.

Greg shifts from one foot to another. He’s holding the shrimp pattern in his left hand. Now, focused. Nicholas directs from the poling platform. Get ready, just give it to him right to his nose. Drop your cast on your back if he turns, we don’t wanna jump him. Ok you see him? You ready? Greg crouches down low, a particularly evolved hunting trait. Something sparkles in his blood. I’ve seen it a million times. He raises the rod, double-hauls on the front, tugging five feet of line at a time. The permit tails sixty feet away, slicing a thin dagger through a sheet of water. Greg fires his shot. Crouched, stripping slowly. Damn, Nicholas breaks in again. He’s moving. He’s onto us. That’s ok, we’ll wade fish him next time. Always encouraging, Nicholas. Positive. Hopeful. A powerful trait in a flats guide. But there isn’t a next time. We drift over an oyster bed. Silent. I smile.

Motoring back to the boat launch as the sun starts to duck behind us, sinking into the Gulf of Mexico, the tide moves out. We check off a list of uninhabited keys as we fly past – Woman Key, Ballast Key, Crawfish Key, Mule Key. The water is flat. The wind is down. We roll over Kingfish Shoals. Saltwater pricks my cheeks, my forehead. The beer in my hand bounces and bubbles over onto the deck of the boat. I don’t even notice. Nobody speaks. We move across the Northwest Channel, approaching Pearl Basin.

Nicholas cuts the motor and the wake pushes us forward hard and we slide up onto a flat. Last shot dude, hop up there.

He’s looking at me. Grab the cuda rod. It’s gray now, and my eyes never really adjusted properly to the flats. But I trust Nicholas, and I can take direction. The turtle grass quietly, slowly, waves at me. Alright dude, 3 o’clock…no no, hold it. 11 o’clock, 50 feet. He’s moving really slow, heading away, you see him? I do not, but I’m already pulling line up off the water and hauling toward 11 o’clock. Let her rip dude, he’s moving! I release the tube fly again, line shoots through my index finger. I tuck the rod up under my arm and strip as fast as I can. Strip strip strip strip dude.

The line goes tight as the barracuda eats.

And somewhere out on Stock Key a rooster pecks at an oyster shell.