Expert-Guided Chokoloskee Fishing with Capt. Randal

Published Date: July 17, 2025
Fishing

Chokoloskee
$300 - $550 price range

Summary

Ready for a laid-back day of fishing in Chokoloskee? Captain Randal's got you covered with a private half-day trip that's perfect for anglers of all levels. You've got options – a quick 2-hour outing for $300 or a longer 4-hour adventure for $550, both for up to two people. Bringing more buddies? No problem, it's just $25 extra per person. The best part? Everything's taken care of. We're talking top-notch gear, fish cleaning and filleting, and even your Florida fishing license. No need to sweat the small stuff. Just show up ready to cast a line in Chokoloskee's rich backwaters and flats. Whether you're aiming to land a big one or just enjoy some time on the water, this trip's got all the ingredients for a great day out. So grab a friend, pack some snacks, and let's hit the water for some quality fishing time.

Expert-Guided Chokoloskee Fishing with Capt. Randal

Chokoloskee Catch of the Day

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

Reel in the Big Ones: Chokoloskee Fishing

Hey there, fellow anglers! Ready to wet a line in some of Florida's richest fishing grounds? Captain Randal's got you covered with a private half-day trip that'll have you hooked from the get-go. Whether you're a seasoned pro or just starting out, this Chokoloskee adventure is tailor-made for a good time on the water. We're talking primo fishing spots, top-notch gear, and all the local know-how you need to land some impressive catches.

What's the Deal?

Here's the scoop: you've got options. If you're pressed for time, the 2-hour trip is perfect for a quick fishing fix. Got a whole morning or afternoon to spare? The 4-hour half-day trip gives you plenty of time to really get into the groove. Both trips are priced for two people, but if you want to bring along some buddies, it's just a small fee per extra person. The best part? Everything's included. We're talking rods, reels, bait, licenses - the works. You just show up ready to fish, and we'll handle the rest. And when you land that monster, we'll even clean and fillet your catch so it's ready for the grill.

Casting in Paradise

Chokoloskee's backwaters and flats are a fisherman's dream. We'll be hitting up some sweet spots where the fish are practically begging to be caught. Depending on the season and what's biting, we might be drifting along mangrove shorelines, poling across skinny water flats, or anchoring up near oyster bars. The technique changes with the target, but you can bet we'll be using everything from live bait to artificial lures to entice those fish. And don't worry if you're new to this - I'll show you the ropes, from how to work a topwater plug to the best way to set the hook when a big red slams your bait.

Fish Tales

Let me tell you, the stories I could share about the monsters we've pulled in these waters would keep you up all night. But it's not just about the size of the fish - it's about the experience. There's nothing like the rush of a snook hitting your line at sunrise, or the fight of a black drum as it tries to wrap you around a piling. Every trip out here is different, and that's what keeps folks coming back time and again.

The Usual Suspects

Redfish are one of our star attractions here in Chokoloskee. These copper-colored beauties love to cruise the flats, tailing in shallow water as they root for crabs. They put up a heck of a fight and are just as tasty on the plate. Fall is prime time for reds, but you can catch them year-round if you know where to look.

Black Grouper and Gag Grouper are the bruisers of the bunch. These guys like to hang around structure, so we'll be targeting reefs and wrecks to find them. They grow big - we're talking 20-30 pounders - and they'll test your arms and your gear. Winter months are best for grouper, but they're around all year.

Snook are the rockstars of inshore fishing. They're wily, they're strong, and they're a blast to catch. We'll be looking for them around mangrove edges and in the passes. Spring and fall are peak seasons, but a good snook bite can happen any time of year.

Black Drum might not be the prettiest fish in the sea, but they make up for it with their power. These cousins of the redfish can grow to over 100 pounds, though we usually target the smaller ones that are better eating. They love hanging around bridges and docks, and they're suckers for a well-presented crab or shrimp.

Time to Get Hooked

So, what do you say? Ready to experience some of the best fishing Chokoloskee has to offer? Whether you're looking to bend a rod, fill the cooler, or just enjoy a day on the water, Captain Randal's got you covered. With everything provided and local expertise at your fingertips, all you need to do is show up ready for action. Don't let another fishing season slip by - book your trip now and let's make some memories on the water. Trust me, once you've fished these waters, you'll be planning your next trip before we even hit the dock.

Learn more about the species

Black Drum

Black drum are the bulldogs of the flats. They're not pretty, but they're tough fighters. Most run 5-30 pounds, but 50-pounders pop up. You'll find them on shallow flats, around oyster bars, and in channels. They love crustaceans, so fresh shrimp or crabs are top baits. Look for them tailing or listen for their distinctive grunting sound. Spring is prime as they school up to spawn. Smaller drum (under 15 pounds) are great eating, but bigger ones get tough and wormy. They're not as glamorous as some species, but put up a great fight on light tackle. My tip: If you see a big school, don't cast right into it. Drop your bait nearby and let them find it. Direct casts often spook the whole group.

Black Grouper

Black grouper are hefty reef fish, averaging 2-3 feet but sometimes topping 100 pounds. You'll find them around rocky bottoms, ledges, and wrecks in 60-250 feet of water. They're ambush predators, so fishing structure is crucial. Use heavy tackle - 80-pound braid isn't overkill. Live bait like pinfish or squid works well, or try jigging big metal lures. Cooler months are best as they move shallower. Grouper are prized for their firm, white meat and put up a brutal fight. Once hooked, they'll try to dive back into their rocky lairs, so you've got to muscle them up quickly. My go-to trick: When you feel that first thump, reel like mad and lift your rod tip to get them away from the bottom fast.

Gag Grouper

Gag grouper are built like linebackers - thick-bodied and powerful. Most run 20-30 inches, but 50-pounders aren't rare. Look for them around rocky bottoms, ledges, and artificial reefs in 60-200 feet. They prefer cooler water, so winter and early spring are prime. Live bait is tops - pinfish, sardines, or squid. Big jigs work too. Gags are notorious for their initial run to the bottom, so lock down that drag. They put up a great fight and the meat is excellent. Regulations change often, so check the current season. My tip: When bottom fishing, keep your bait moving. A slow retrieve often triggers strikes better than letting it sit.

Redfish

Redfish are a popular target here in Chokoloskee, known for their distinctive black tail spot. Most run 20-30 inches, but trophy fish over 40 inches aren't unheard of. You'll find them tailing in shallow grass flats and mangrove shorelines, especially on incoming tides. They love crustaceans, so live shrimp or crabs are top baits. Artificials like gold spoons work great too. Redfish put up a strong fight and make excellent table fare. Spring and fall are prime seasons as water temperatures are ideal. When sight fishing, look for their copper-colored backs and tails breaking the surface. My tip: If you spot a school, cast beyond them and slowly drag your bait into their path. They spook easily, so a stealthy approach is key.

Snook

Snook are the rockstars of our backwaters. Sleek, powerful, and smart, they're a blast to catch. Most run 24-34 inches, but 40-inchers aren't unheard of. You'll find them around mangroves, docks, and creek mouths. They love structure and current. Live bait like pilchards or pinfish is hard to beat, but artificial lures work great too. Snook are temperature sensitive, so spring and fall are prime as they move in and out of the backcountry. They're famous for their acrobatic jumps and blistering runs. The meat is excellent, but highly regulated. My top tip: Fish the shadow lines on sunny days. Snook often hide in the shade, ambushing prey that swims by.

About the Bobby Jones Cottonmouth

Vehicle Guest Capacity: 4

Manufacturer Name: Suzuki

Maximum Cruising Speed: 40

Number of Engines: 1

Horsepower per Engine: 115

Get ready for a laid-back fishing adventure in beautiful Chokoloskee! Whether you're a seasoned angler or just starting out, this private trip is perfect for enjoying the area's rich backwaters and flats. Choose between a quick 2-hour outing or a more relaxed 4-hour half-day trip, both designed for up to two people. Need to bring more friends? No problem - it's just $25 extra per person. The best part? Everything's taken care of for you. We provide all the quality fishing gear you'll need, handle the catch cleaning and filleting, and even sort out Florida fishing licenses for everyone. No need to stress about permits or equipment - just show up ready to cast a line and have a great time on the water. With a knowledgeable guide leading the way, you're in for a fun, stress-free day of fishing in one of Florida's most beautiful spots.

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