Kayak Fishing the South Side of Winter Park Chain

KAYAK FISHING REPORT

Pedal. Cast. Smash. Repeat.

Picture yourself pedaling along in your fishing kayak. You’ve just pushed through a beautiful canal lined with ferns, palms, cypress—a true assortment of jungle foliage. You’re feeling pretty good about the soft plastic buzzing topwater frog/gator imitation bait you’ve tied on. You’ve already landed a handful of fish skipping it under docks and along a seawall in the canal.

As you emerge into an open lake, you’re faced with a decision: head due north, or take a left and push west along the south side of Lake Osceola. You stayed north last time you were here—two years ago—so today, you decide to mix it up.

Before you lies a vast field of lotus pads, and just beyond, giant oaks stretch their shade out across the water. The lake is stunningly clear, with pads and eelgrass as the main sources of cover.

You know what time it is. Rudder up. Kick fins latched. Paddle out. You stand with rod in hand, paddle resting across the bow of your trusty steed—the Hobie Outback. It’s quiet. Stable. A true amphibious weapon. Confidence builds.

You rear back and unleash a slip cast way up under the oak shade. Your bait smacks a cypress stump and you burn it back. The ripples grow. You hit the edge where the water deepens and the lotus pads thicken.

Then it happens.

BANG!

Like a small cannonball, an explosion rocks the water. You mutter the sacred phrase under your breath:

“Eat my frog.”

Three words whispered to no one.

You set the hook.

Immediately, you know—it’s a good one. Not a record-breaker, but a solid Florida bass. Then it wraps up in lotus pad stems. Game over?

Not even close.

Moments later, you’re paddling one-handed, half-submerged in belly-deep water, rod in the other hand. You grab the fish. Victory.

Worth it? Absolutely.

But no time to celebrate—you’ve only landed your fourth fish. You’ve got about 22 more before calling it a day.

Let the games begin.

Happy Monday, Spacefish!

This week’s report is all about the south side.

Not that south side. Sure, the new Pope (or as my buddy Bobby Norton says, “Da Pope”) is from Chicago—but we’re not talking about the Holy Father or the Windy City today.

We’re talking about the stunningly gorgeous Winter Park Chain, just north of Orlando.

Launch Spot & Lake Breakdown

For this trip, I launched from Dinky Dock Park
📍 410 Ollie Ave, Winter Park, FL 32789

My goals:

Complete the Fast Food Challenge from last week’s report
Catch fish in every lake and every canal on the chain
Rack up a high number of bites

Pushing through the fern canal into Lake Osceola.

I started on the north side of Lake Virginia, catching two bass by skipping the Bitters Buzz’n Gator under docks. Already checked off Virginia, I pushed north through the fern canal into Lake Osceola, spending most of the day there. Later, I punched back through to Virginia, moved south a few hundred yards, and entered the Genius Canal, linking Virginia to Lake Mizell.

Caught one quickly in Mizell. Then another in the canal. At that point, I’d landed 25+ bass, was feeling gassed, and ready to call it a successful day.

Two Confidence Baits That Crushed

It had been a while since my last dedicated bass trip. I’d been catching bass while chasing tarpon in the backwaters of the Indian River Lagoon—very different from lake fishing.

My approach: power fish with confidence baits that let me cover water and fish all depths. I used two:

Bitter Skip Shad (Houdini) — rigged weightless & weedless on a 3/0 EWG
Bitters Buzz’n Gator (Watermelon Red Pearl) — also weightless & weedless on a 3/0 EWG

I started with the topwater Gator, burning it back, skipping it under docks, and buzzing it over lotus pads. It drew exciting surface strikes.

The Skip Shad (fluke-style bait) was the top producer. It skips into tight spots, casts long, and can be worked a dozen ways—twitched, deadsticked, walked subsurface – it really is a dealers choice type of bait.

I love a speedworm (really, really do), but the fluke might be the GOAT—not just for bass, but also snook, trout, and even tarpon.

Results:

23 of 26 bass on the Gator and Skip Shad
3 on a speedworm
Sometimes Plan A works. Stick with it.

Gear Talk: Reliable Kayaks & Secret Weapons

As I tell my football players:

“The best ability is availability.”

Same goes for kayaks. You don’t need the most expensive rig—just a reliable one.

For the past 18 months, I’ve been running used Old Town and Hobies from Kayaks By Bo—part of their test fleet. With the money saved, I’ve been able to invest in rigging, customizations, and repairs.

The real MVP?

Andy.

He’s the kayak whisperer. Rudders, cords, pedal drives—you name it, he fixes it.

One reason I love Kayaks By Bo: they’re not just a place to buy a kayak. They’re a family-run operation that offers repairs, rigging, and great service.