Pro Anglers' Chokoloskee Backcountry Adventure

Published Date: August 29, 2025
Fishing

Chokoloskee
$300 - $550 price range

Summary

Chokoloskee's backwaters are a playground for skilled anglers, and this half-day trip is designed to make the most of your time on the water. For four hours, you'll explore the productive flats and hidden spots that make this area a top fishing destination. Captain Randal provides everything you need - from premium gear to licenses - so you can focus on the action. With room for two guests (and the option to add more), it's perfect for buddies looking to test their skills against a variety of fish species. The shallow waters here are known for consistent bites and the chance to land some impressive catches. Whether you're sight-casting in crystal clear shallows or working deeper channels, you'll have plenty of opportunities to put your angling skills to the test. At the end of the day, your guide will clean and fillet your catch, capping off a well-rounded fishing experience in one of Florida's most unique coastal environments.

Pro Anglers' Chokoloskee Backcountry Adventure

Backwater Battles

Had a good day on the water with these two guys and the young man’s 30 inch snook

Two nice snook that I caught myself today in about 30 minutes there about 26 inches long

Neil with a nice Goliath grouper

Chokoloskee's Inshore Fishing Paradise

Ready to test your skills in one of Florida's most productive inshore fisheries? Captain Randal's Chokoloskee fishing trip is tailor-made for anglers who know their way around a rod and reel. This half-day adventure takes you deep into the backwaters and shallow flats where the big ones lurk. With everything from gear to licenses covered, all you need to bring is your A-game and a desire to tangle with some of the Sunshine State's most sought-after species.

What to Expect on the Water

This isn't your average tourist fishing trip. We're talking about 4 hours of non-stop action in the labyrinth of mangrove islands and grass flats that make Chokoloskee a top-rated fishing destination. Captain Randal's got you covered with top-notch gear and local knowledge that'll put you on the fish fast. Whether you're sight-casting to tailing redfish or working the deeper cuts for gag grouper, every cast could be the one that lands your personal best.

Techniques That Turn Heads

Out here, versatility is key. We might start the day throwing soft plastics along mangrove shorelines for snook, then switch to live bait for black drum in the deeper holes. Captain Randal's always got a few tricks up his sleeve, like using cut bait to entice those big black grouper out of their hidey-holes. You'll get to try a mix of light tackle techniques that'll challenge even the most seasoned anglers. And when you hook up, be ready – these Chokoloskee bruisers don't go down without a fight!

Species You'll Want to Hook

Redfish: These copper-colored bulldogs are a staple of Chokoloskee fishing. Known for their powerful runs and distinctive tail, redfish love to cruise the shallow flats in search of crabs and small fish. The best part? They're here year-round, with fall being prime time for big schools of oversized reds.

Black Grouper: The kings of structure fishing, black grouper are ambush predators that hang around rocky bottoms and reefs. They're not easy to fool, but when you do, hold on tight! These guys can top 100 pounds and will test your arms and your drag. Winter months are usually best for targeting these brutes.

Gag Grouper: Cousins to the black grouper, gags are another hard-fighting bottom dweller. They're known for their aggressive strikes and tendency to dive for cover as soon as they're hooked. Look for them around underwater structure and prepare for some serious rod-bending action. Peak season is typically fall through early winter.

Snook: The prized game fish of Florida's southwest coast, snook are as challenging as they are delicious (catch and release only in Chokoloskee). These silver-sided predators are masters of using structure to their advantage, so accurate casts are a must. Spring and summer are prime time for snook fishing, especially around mangrove shorelines and oyster bars.

Black Drum: Often overlooked but never underestimated, black drum can grow to massive sizes in the Chokoloskee backcountry. These cousins of the redfish are bottom feeders with a soft spot for crustaceans. They're known for their powerful, thumping fights and distinctive chin barbels. You can target them year-round, but winter tends to see the biggest concentrations.

Why Anglers Keep Coming Back

It's not just about the fish – though let's be honest, that's a big part of it. Chokoloskee offers a fishing experience you can't find anywhere else. One minute you're casting into a maze of mangroves, the next you're drifting over crystal-clear flats. The scenery's wild, the fishing's hot, and with Captain Randal at the helm, you're in for a day that'll have you planning your next trip before you even hit the dock.

The Captain's Touch

Speaking of Captain Randal, he's not just another guide with a boat. This guy eats, sleeps, and breathes Chokoloskee fishing. He's got eyes like an osprey when it comes to spotting fish, and he knows every nook and cranny of these waters. But what really sets him apart is his ability to read the conditions and adjust on the fly. Tide not doing what it should? No problem. Fish being finicky? He's got a Plan B (and C, and D) ready to go.

Gearing Up for Success

Leave your tackle box at home – Captain Randal's got all the gear you need to put fish in the boat. We're talking top-of-the-line rods and reels, paired with the right lures and bait for whatever's biting. From light spinning setups for sight fishing to heavier gear for battling those grouper, you'll be fishing with equipment that's up to the task. And don't sweat the licenses – they're all included in your trip.

More Than Just Fishing

Sure, the fishing's world-class, but there's more to a Chokoloskee trip than just wetting a line. You're in the heart of the Everglades, one of the most unique ecosystems on the planet. Keep your eyes peeled for wildlife – we're talking ospreys diving for fish, dolphins playing in the wake, and maybe even a manatee or two if you're lucky. It's the kind of natural beauty that makes even the slowest fishing days worthwhile.

The Nitty Gritty

Let's break down the details. This half-day trip runs for 4 hours and is priced at $550 for up to two anglers. Got a bigger crew? No problem – additional guests can join for just $25 each. Captain Randal takes care of everything from gear to licenses, and he'll even clean and fillet your catch at the end of the day. Just remember, the deposit's non-refundable, so make sure you're good to go before you book.

Time to Book Your Spot

If you're an angler who's always looking for that next great fishing experience, Chokoloskee is calling your name. With Captain Randal's expertise, top-notch gear, and a fishery that's teeming with life, this trip checks all the boxes for a day on the water you won't forget. Whether you're after that bull redfish of a lifetime or just want to bend a rod on whatever's biting, now's the time to lock in your date. The fish are waiting – are you ready to meet them?

Learn more about the species

Black Drum

Black drum are the bulldogs of the flats, averaging 5-30 pounds but capable of topping 80. You'll find them rooting around oyster beds and muddy bottoms in 2-6 feet of water. Spring is prime time as they school up to spawn, but we catch them year-round. These guys aren't the prettiest fish, but they pull like freight trains. Fresh crab or shrimp on a circle hook is hard to beat for bait. When you feel that telltale thump, give them a second before setting the hook. Black drum fight deep and dirty, so be ready for a workout. Here's a local tip: listen for their distinctive croaking sound to locate schools. The smaller ones under 15 pounds are great eating, with sweet, white meat. Bigger ones can be tough, so we usually release those to fight another day.

Black Grouper

Black grouper are ambush predators you'll find lurking around structure in deeper water. These hefty fish average 20-30 pounds but can top 100. They're a prized catch, known for their power and tasty white meat. We target them around reefs, ledges and wrecks, typically in 60-250 feet. Spring and fall are great seasons as they move to shallower haunts. Live bait is key - big pinfish or blue runners work well. Once hooked, get ready for a battle. These guys head straight for their rocky lairs, so you need heavy tackle and a locked-down drag. Here's a pro tip: when you feel that first thump, reel fast and lift your rod to pull them away from structure. Land a big black grouper and you've got serious bragging rights - and a cooler full of premium fillets.

Gag Grouper

Gag grouper are hard-fighting fish that'll test your skills and gear. They average 10-20 pounds but can reach 50+. You'll find them around rocky bottoms, reefs, and ledges in 60-200 feet of water. Spring and fall are prime seasons as they move shallower. Live bait is the ticket - pinfish or sardines work great. When you hook up, be ready for a tug-of-war. These guys make a beeline for their rocky homes, so use heavy tackle and keep that drag tight. Here's a local trick: when you feel the bite, reel fast and lift your rod to pull them away from structure. Gags put up an awesome fight and make excellent eating. Landing a big one is a real accomplishment - you'll definitely feel it in your arms the next day!

Redfish

Redfish, or red drum, are a favorite inshore target here in Chokoloskee. These copper-colored bruisers average 20-30 inches but can grow over 40. Look for them tailing in shallow flats or cruising mangrove shorelines, especially on incoming tides. Redfish put up a great fight and make excellent table fare. Spring and fall are prime seasons, but we catch them year-round. They'll take live bait, but sight-casting with artificial lures is a blast. Gold spoons are my go-to - the flash mimics baitfish and really gets their attention. When you hook up, be ready for some drag-screaming runs. Just remember to keep your rod tip up and let them tire themselves out. There's nothing quite like the thump of a big red taking your bait in skinny water.

Snook

Snook are one of our prized gamefish here in Chokoloskee. These sleek, powerful fish average 24-34 inches but can top 40. You'll find them lurking around mangroves, oyster bars, and dock pilings. Spring and fall are prime, but we catch them year-round. Snook put up an amazing fight, with blistering runs and acrobatic jumps. They're also excellent eating when in season. Live bait like pilchards or pinfish works great, but fooling one on artificial lures is a real thrill. My go-to is a white paddletail jig - work it slowly along mangrove edges. When you get a hit, let the snook run a bit before setting the hook. Then hold on tight and keep them from wrapping you around structure. Landing a big snook is a badge of honor for any angler.

About the Bobby Jones Cottonmouth

Vehicle Guest Capacity: 4

Manufacturer Name: Suzuki

Maximum Cruising Speed: 40

Number of Engines: 1

Horsepower per Engine: 115

Hop aboard for a laid-back yet rewarding fishing trip in Chokoloskee's diverse backwaters. We'll cruise the shallow flats and mangrove-lined channels in search of the area's many gamefish species. This half-day outing is ideal for experienced anglers looking to maximize their time on the water and put their skills to the test. With room for two guests and top-notch gear provided, you can focus on the fishing without any hassle. Your knowledgeable guide will lead you to prime spots while sharing local insights. When you land a keeper, we'll clean and fillet your catch so it's ready for the dinner table. Whether you're after snook, redfish, or whatever's biting, Chokoloskee's productive waters offer plenty of action in a beautiful natural setting. It's a great way to spend a morning or afternoon doing what you love in one of Florida's fishing hotspots.

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