Why Kayak the Keys?
There are easier ways to fish the Florida Keys. You could hire a flats guide with a Hell’s Bay skiff and have tarpon located for you. You could stay in a comfortable hotel in Islamorada and drive to different launch spots each day. You could be sensible. But my buddy Derek and I decided that four days of paddling, camping on remote islands, and targeting tarpon and permit from sit-on-top kayaks was the only way to truly experience the backcountry. We were half right and completely sunburned.
We launched from Key Largo in mid-May, loaded down with camping gear, fishing tackle, and approximately seventy percent of the sunscreen we actually needed. Our plan was to paddle west through Florida Bay, camp on Nest Key the first night, work our way to Rabbit Key Basin for the tarpon, then loop back through the backcountry lakes chasing permit. Four days, roughly 45 miles of paddling, and hopefully some fish of a lifetime.
Day One: The Reality Check
The first thing you learn kayaking the backcountry is that wind matters more than tide. We launched into a 15-knot southeast breeze that turned every stroke into a fight. By the time we reached Nest Key, seven miles later, my shoulders were burning and my spirits were sinking. We made camp on the chickee—a raised wooden platform that serves as the only legal camping in most of the backcountry—and watched the sunset paint the mangroves orange.
That evening, we waded the nearby flat as the light faded and I hooked my first backcountry tarpon. It wasn’t huge—maybe twenty pounds—but it jumped six times before throwing the hook. I stood in knee-deep water, rod still bent from the memory of weight, and realized why people get obsessed with this fishery.
Days Two and Three: The Grind and the Glory
The middle days blurred together in a haze of paddling, casting, and reapplying aloe vera. We found tarpon rolling in Rabbit Key Basin on the second morning, and I landed a fish around fifty pounds after a 25-minute fight that left my arms shaking. Derek hooked a permit on a small crab fly—his first ever on fly—but it cut him off on a coral head before he could get it to the kayak.
The permit became an obsession. We spent all of day three sight-casting to tailing fish on a flat near Johnson Key, and I learned more about permit refusals in eight hours than I had in years of reading about them. These fish see everything. They feel your kayak’s shadow from fifty feet away. They’ll eat a crab that lands two feet in front of them and completely ignore one that lands three feet away. It’s maddening and addictive in equal measure.
The Sunburn Situation
By day three, both of us looked like boiled lobsters despite wearing long sleeves, buffs, and wide-brimmed hats. The sun reflects off the water, bounces off the kayak hull, and finds every gap in your defenses. My feet, protected only by water shoes, were blistered across the tops. Derek’s neck, where his buff had slipped, was peeling in sheets. We went through two tubes of sunscreen and should have brought four.
Day Four: The Permit Victory
On the last morning, with our bodies broken but our spirits stubborn, I finally got my permit. It was feeding in turtle grass, tailing with that distinctive black sickle cutting the surface. I made the cast—a Merkin crab on a 10-weight—and watched the fish turn, follow, and eat. The hookset was pure reflex, and then everything went sideways as the permit tried to reach the horizon.
I landed that fish after a fight that took me into my backing twice. Twenty-three inches, maybe seven pounds, and worth every blister and sunburn. Derek snapped a photo, I revived the fish carefully, and we began the long paddle back to Key Largo.
Would I Do It Again?
Absolutely. But next time, more sunscreen, lighter camping gear, and maybe a slightly shorter route. The Keys backcountry from a kayak is fishing at its most raw and rewarding. You earn every fish, every sunset, every memory. Just budget an extra week afterward for your skin to heal.
