The swell bobbed our skiff in a consistent rhythm, and the only thing that kept me awake was the occasional larger wave that sprayed over the gunwales. We’d awoken early, downed either Diet Coke or Red Bull, and left the relative safety of the backcountry for the oceanside flats of the Florida Keys.
Unlike all the Instagram reels and YouTube videos I watched in anticipation of this trip, we didn’t have glassy water and no other boats on the horizon. The dock, back towards the Gulf, was protected from the wind by smaller keys, mangrove islands, and canals. Out here, with nothing between us and Cuba except a good deal of sharks, the wind howled in a way that didn’t seem possible. From the truck, on U.S. Highway 1, the ocean looked relatively calm.

That gentle wake I saw on the drive to the boat ramp turned out to be enough chop and movement—especially in a skiff—to make me wonder if any fish is worth hours of sitting, waiting, and forced spinal compression.
This was supposed to be our best weather day, too.
The day before featured nonstop rain, winds consistently blowing out of the east at 20 miles per hour, and none of the visibility you need to chase tarpon (our target species), permit, or bonefish. Instead of fly fishing, we threw barracuda tubes on the flats. I hooked into one that peeled off line with all the speed and grace of a rocket. It jumped and threw the hook back at the boat before I fully realized I had something that angry on the line.
Later, we bounced jigging spoons in a deep channel, where jacks and ladyfish smacked them consistently. The problem there was that the sharks kept eating the smaller fish off our lines. One shark even took the jigging spoon, ran a few hundred yards, then casually swiped the 20-pound braid with its tail and sliced it clean.
By day two of the trip, I was tired, wet, sore, and still not used to the humidity of the Keys. I’m a native Westerner, born and bred in the Rockies. I don’t know how anyone, on either coast, handles the humidity, although I suspect losing some weight would make me a bit more comfortable.
With calmer winds and no clouds in the forecast, day two looked like our best bet to find and cast to the tarpon we were chasing. Max, my good friend and the fearless editor-in-chief here at Flylords, perched on his poling platform, scanning the choppy water for a string of tarpon. I did my best to look, too, but this was my first saltwater trip. I only knew that I was looking for dark shapes moving in a line, and not much else.
When Max thought he saw something off to my left, I threw a cast without thinking, and promptly buried a tarpon fly in the back of my head. It didn’t go past the barb, thankfully, but it drenched my favorite sun hoody in blood. At least it was evidence that I was doing something, though.

I’d expected a good deal of waiting and watching, from my talk with Max before the trip, and reading stories of tarpon fishing. You stake a claim on a flat, watch for cruising fish, and hope you don’t botch the cast when you get the chance. It’s a demanding style of fishing, because unlike trout fishing back home in Wyoming, you have to stay alert without the consistent motions of casting, retrieving line, and freeing your flies from branches to help.
The first time I read Tom McGuane’s essay about permit fishing, where he describes the wait between hooking fish at the longest silence, I thought I understood what he meant. It’s like any other long stretch of not catching fish, right?
Not quite.
The wind, the salt spray that dries and cakes your face, the sun, the humidity, the constant rocking of the boat, the slight desperation that creeps in by the middle of day two because you still haven’t seen a tarpon, the notion that perhaps you’re casting after a fish that doesn’t exist—there’s not quite a corollary for all of that in trout fishing.
Before we broke for a late lunch on day two, we tried one more flat that looked promising. We’d left the oceanside flats and headed into the backcountry of the Keys, looking for some shelter from the wind. There wasn’t much, but we had a bit more visibility, and my meager casting abilities weren’t as obvious.
That’s when we saw the first tarpon of the trip—a huge shadow that shot out from a hole of seaweed and sand, where it was laying up, basically asleep. The fish was big—Max said probably in the 80-100 pound range—and it shot off with enough speed to make me wonder if I was really up for catching one.
That turned out to be the only tarpon of the trip, too. In three days of fishing, I never got a shot at a fish. They weren’t in their usual backcountry haunts, and the driving wind made it almost impossible to pole the oceanside flats. Perhaps most telling was the fact that No Name Pub was full of other tarpon anglers at two in the afternoon, all of whom had thrown in the towel. One person said they’d seen another boat, probably a guided trip, hooked up, but that was all the success to share.
I’ve been skunked plenty, and I know it’ll happen again, and probably soon. But there’s a difference between not catching anything, and getting thoroughly beaten up, the latter of which is what Max and I experienced. Max took it all in stride; he lives in Florida, he’s caught a few tarpon in his day, and he’s a much better angler than I am.
I tried not to internalize the failure too much, but I couldn’t shake the feeling that maybe I’d taken a bite at this apple before I was quite ready. Then again, I don’t know much of anything that’s going to prepare you for three days chasing tarpon in the Keys. It’s a one-of-a-kind experience, and even though I didn’t sniff a tarpon, I completely understand the draw it has on people now.
I’m already planning another trip.

Fifteen years ago I spent $1300 for two days of guided fishing in Florida, One day the only tarpon I saw wouldn’t eat. The other day I saw no fish at all.
I’ve never been back to the state.