Wind, tailing redfish, and the grind that makes it all worth it

First Light Magic

All the best fishing trips start at first light. There’s something about pulling into the boat launch in the dark—air already hanging at a humid 70 degrees, the quiet hum of outboards idling, and the soft glow of navigation lights dancing on the water. The moment you step out of the car, the salty scent of the ocean hits you, and you just know… it’s going to be a good day.

As we eased out from the dock in the no-wake zone, I found myself appreciating the forced calm. It slows everything down, lets you soak it all in. Dolphins were already working the shallows, their dorsal fins cutting through the still water as the sun started to rise and the birds began to stir. Everything was coming alive.

And whatever happened next, I knew we were already winning.

The Crew and the Glide

This year, we teamed up with a solid crew—Rich Doherty of Fish Responders Charters, Rick “2 Degrees” Hilliard of Weird Waters Fishing Charters, and Rick’s buddy Jacob, the owner of Clarity Lures. Stac and I were fishing with Rick in his brand new Eastcape Glide. We were the guinea pigs—Rick wanted to see how shallow the boat would float with three anglers and how stable it’d be underfoot.

Rich and Jacob took Rick’s other skiff and set off to explore different water.

At first, the conditions were perfect. Barely a whisper of wind. But by the time I stepped up on the casting deck, it picked up fast. This was going to be a test—for Rick’s poling, and for my casting. Stac, who was more than ready to fish, made the call to sit it out rather than fight the wind all day with a fly rod.

Naturally, the calm days leading up to this one had been textbook. Rick had put fly anglers on quality fish and even helped someone complete an inshore slam—redfish, sea trout, and black drum.

For me, I had yet to land a sea trout or black drum on fly, so I was excited just to have a shot.

Blind Shots and Hunting Tails

We started at a spot where trout had been holding. It was slightly deeper—maybe a few feet, as opposed to the skinny inches we’d chase redfish in. We blind casted for a bit, but it wasn’t long before Rick shifted gears and started hunting.

And that’s exactly what it is—hunting.

The three of us scanned every inch of water—from the edge of the flat to right in front of the skiff. That’s where we kept spooking fish. Unlike last year, there weren’t tails waving in the air to give them away. Just subtle movement, flashes, wakes—and wind. It was a challenge.

But we kept grinding.

Shortly after leaving the trout spot, I hooked into a redfish. We’d just cast at a small group, and I had honestly given up on them. I stopped stripping and then—bam—felt the grab. I set hard. Maybe too hard. But I wasn’t about to miss this one.

It wasn’t a giant, but it broke the ice. The skunk was off the boat. That one fish changed the tone of the whole day.

Leader Lessons and Wind Wars

Earlier that month, Rick had attended a fly fishing school with Flip Pallot and Mad River Outfitters. Not that he needed it—Rick’s a solid guide—but he’s always looking to refine. One tip from Flip stood out: use 15-foot leaders for Mosquito Lagoon fish.

I was game to try it. But I’ll be honest—there’s a time and place for a leader that long, and a windy day with a light chop isn’t it. The fish aren’t as spooky when the surface is broken. I don’t fish redfish regularly, but I chase shallow-water carp all the time, and they’re just as picky. In my opinion, if you’re new to fly fishing, don’t even try it. You’ll just end up frustrated.

With a couple hours left in the day, I cut my leader down to 9 feet. We had several fish come in close—within a few feet of the boat—and a 15-foot leader just doesn’t work at that distance. After the switch, we focused on black drum. Rick poled straight into the wind (and I cast straight into it), giving me a few solid looks. No eats, but seeing those fish up close was worth it.

One Fish, Many Reasons

We ended the day with just the one redfish in the boat, and another that came unbuttoned. But for me, it was still a great day on the water.

There’s just something about this fishery I can’t get enough of. I love the challenge of it—the stealth, the patience, the reward. I love how spooky the fish are, how technical the presentations can be, and how, if everything lines up just right, they’ll eat a fly without hesitation.

And beyond the fish, there’s the life—dolphins, manatees, birds—it’s nonstop action in every direction.

If you ever find yourself in the Orlando area, do yourself a favor: take the short drive east to Mosquito Lagoon. Or better yet, just make it your whole destination.