The BEST of KEY WEST in 5 days!

"The Best of Key West in 5 days"


*** As featured in the Apr / May issue of Mexico’s top Sport Fishing Magazine = Con Cana y Carrete

By: First Mate Deidra Bridger with Captain Bo Johnson

I live in Southwest Florida where fortunately summer comes early for my solar powered soul. As luck would have it, this year the sunshine rays kissed me even sooner! The beginning of February, this First mate was Key West ‘bound!! I helped my Captain, Bo Johnson, gather the tackle, rods, and gear and load up the F-250 truck and 22 foot Lake and Bay boat and away we went!! The 5 hour drive flew by and just as the sunset caressed the Key West horizon, we pulled up to local guide and friend, Captain Bryan (Bear) Holeman’s home. The 5 day adventure would kick start with 2 days of pre-fishing followed by 3 days of fishing our clients who were flying in from Kansas.

The first day, Capt. Bo, Capt. Bear, and First Mate D headed to the boat ramp mid-morning. The nice thing about sight fishing is that you need ample light so getting on the water at the crack of dawn is not necessary. While idling out, we strategized our scouting agenda and decided on cobia, permit, barracuda, and sharks! Permit would require picking up crabs at the marina, so we idled over, stocked up, and we were off! We ran 35 miles off the west side of Key West to our first stop – a wreck located southwest of the Marquesas Islands.

Cobia conquest

We timed our conquest for cobia in synch with the slowing tide. This pelagic species would be on the surface and there is nothing like watching them eat! With fish from 10-60 lbs in the crystal clear blue waters, it was impossible to miss the wolf packs circling the shipwreck. We observed multiple schools on all sides of the wreck and decided to ambush the biggest school. Capt. Bo and I got ready and 1.. 2.. 3.. we cast. Wham, doubles! What a rush! It was a game of balance – under and over, and around the boat we went! Capt. Bo, Capt. Bear and I all took turns running the boat, sighting the schools, and catching and landing the fish.

The nice thing about a school of cobia is if one gets hooked, others will follow. So once one angler hooks up, a good strategy for the second angler is to present a lure to the fish following his schoolmate. Cobia are great game fish: they almost always eat, put up an intense fight, and they make succulent table fare. We found our success using a 12-17 lb spinning outfit comprised of American Rodsmith rod and Shimano 4000 reel rigged with just 15 lb braid and 40 lb fluorocarbon leader, and secured Al Gag’s 8 inch red Whip-It eel onto his custom jig head.

Permit crusade

After successfully landing several 15-50 lb cobia, it was time to fulfill Capt. Bo’s life long crusade for that trophy permit! A 15 minute run east / northeast took us to another wreck recognizable by 5 tall wood pilings. We idled in and cut the motor. Capt. Bo jumped to the bow to run the trolling motor in search of the schools of permit with Capt. Bear at his side. I quickly grabbed the same spinning outfit used for the cobia but tied on a 20 lb fluorocarbon with a 1/0 circle hook and rigged a silver dollar sized crab. Just as I finished rigging the rod, Capt. Bear spotted a nice school of about 100 permit about 7 feet down in the water column. We positioned the boat to ensure an accurate cast would enable the crab flow down-tide to the awaiting permit. Capt Bo watched his crab pass the first part of the school. CRUNCH! The permit took the crab!

Capt Bo waited for the line to pull tight then lifted the rod, securing the circle hook in his adversary’s mouth. The fight was on! Then I spotted a school of cobia heading for our bow. I grabbed my rod and cast in front of the school, ripping Al Gag’s red Whip-It eel on the retrieve. The head cobia peeled out giving chase to my bait! I sped my retrieve… twitch, twitch… STOP… he ate it!! WOOHOO!! After a short battle, Capt. Bear landed my 20 lb cobia with the Boga grip and I got ready to tail Capt. Bo’s permit. What a great feeling to play a part in his goal achievement of a sought-after trophy!

Shark saga

During the fight for Capt. Bo’s permit, we noticed multiple Bull sharks chasing his fish. It was time for me to land a trophy fish of my own! We pulled off the wreck 50 yards, dropped the Sea Claw anchor, and my heart began racing with anticipation. Capt. Bo cut a few pieces of chum and hung them over the side. I grabbed an American Rodsmith conventional rod rigged with an Accurate 665 reel spooled with 100 lb braid (main line) and terminal tackle comprised of a 3 foot shot of 100 lb fluorocarbon tied to a swivel and about 18 inches of #7 single strand wire and a 11/0 circle hook tied with a haywire twist. To finish off my rig, I cut a 6 inch steak cut out of a Jack Crevalle for bait. I pitched the morsel 20 feet behind the boat where the sharks were circling. 11 seconds later, the clicker went off!!! I fed him10 – 15 yards of line before engaging the reel and set it to strike. My line peel off at such amazing speed that the water mist looked like smoke!! We had to chase this monster so Capt. Bear pulled the anchor while Capt Bo strapped a fighting belt around my waist then fired up the motor. We regained the 200 + yards of line by chasing down the fish then it was a game of 1 on 1… D vs. Bull shark…who would win!??

After 30 minutes of grueling down and dirty tug-o-war, we got our first glimpse of just how massive this fish was. I worked him over to Capt Bo alongside the gunwale. We decided it was an opportunity to get a pic of a lifetime so Capt. Bo tailed the shark and together with Capt. Bear, they pulled the mighty shark aboard for a photo.

Within minutes, the fish was released happy and unharmed. What a day!! With huge smiles of satisfaction on our faces, we made the return run back to Key West, arriving at the dock just as the sunshine fireball sank into the horizon.

On the second day of pre-fishing, we captured underwater footage of a tarpon laid up alongside the pilings while idling out. Key West is one of the 1st stops for tarpon on their northbound migratory voyage. With that, our first fish on the day’s agenda was decided. In 10 minutes, we stopped to check a spot for tarpon. All eyes were peeled looking for a free jump, a bust, or a roll of the Silver King. All of these are easy indications how to position your boat to set up your drift. In the first 5 minutes, we noticed the majority of the fish located on a break (where the tide flushes on both sides of a bank). These fish were saturated on the west side of the bank where water depth would rise from 10ft up to 3 ft back down to 10 ft. The tarpon had positioned themselves so they could use the break as an ambush point for crabs, mullet and threadfins. Our baiting strategy consisted of 2 crabs tied on 5/0 Owner’s Mutu circle hooks and one Al Gag’s 8 inch Whip-It eel in watermelon secured on his custom jig head, both attached to 80 lb fluorocarbon leader and 60 lb braid for main line. As we neared the “happy” fish, Capt. Bo and Capt. Bear threw out crabs and I decided to sight cast with the eel lure. Depending on which direction the fish rolled, I would adjust my cast to optimize their opportunity to eat. I noticed a few followed my eel to the boat but turned before inhaling it. After a dozen casts, it was clear this lure commanded attention of the tarpon. Any given cast could result in a fish weighing up to 200 lbs on the other end of my line! 20 min went by and finally a tarpon decided to inhale the eel and skyrocketed into the air! No doubt in my mind why they call this mighty fish the “Silver King”. On the second jump, he threw the lure. Tarpon 1, Deidra 0. The challenge of Tarpon fishing is 1) to entice them to eat, 2) to keep them on the hook, and 3) to land them! When all three come together, it’s a trophy of a lifetime. When they don’t, it’s still a rush of a lifetime.

Barracuda Ambush

After playing with the ‘poons’, we turned our attention to the crystal clear shallow flats surrounding Key West. Idling a mere 200 yds to the edge of the flat, we dropped the 36-volt motor guide. As far as Capt Bo and I are concerned, the barracuda species is an underrated game fish. They hit with precise accuracy and peel drag with lightening speed, making many leaps into the air! The ‘cuda are particularly a great adversary on light tackle such as we used: 12-17 lb spinning outfit rigged with just 15 lb braid and 40 lb fluorocarbon leader with a short piece of wire, secured to one of Al Gag’s jig heads and his red 8 inch Whip-It eel.  The ticket for enticing a ‘cuda strike is to make a long cast past the ‘cuda, then rip the lure through its peripheral vision on your retrieve. As the lure nears, the ‘cuda instantly lights up and charges! There it is.. STRIKE, and he’s ON! Capt. Bo, Capt. Bear and I enjoyed several adrenaline rushes with the fanged fish that tend to strike only a few feet from the boat. One of the highlights occurred when a ‘cuda smacked the lure at lightening speed only inches from Capt. Bo’s hand that held our under water camera. WOW!!!

Thrash on the Flats

After the tide stopped, turned, and began to go out, we decided to set up for sharks on the edge of a beautiful huge bowl surrounded by a mile long half moon shaped flat. Once reaching our desired depth of 3 feet, I staked off the boat by lowering our Power Pole and Capt. Bo set the chum overboard. As the water flushed from the flats into the bowl, the chum scent enticed several sharks within minutes. The majestic creatures began to make wide sweeps honing in on the bait. Once pin-pointed, they speed their attack creating a v-shape push in the water. It isn’t long before the 1st shark found the bait. His long slender tail protruded the top of the water as he went nose down to snatch the bait. Shark onnn!!! 250 yards of line later, the fish was finally turned and I began the battle to get my line back! So with a pumping motion, I continuously pulled up and reeled down. As the shark neared, we identified him to be a Lemon shark. What a beautiful sight to observe him thrash in the lush grass flats. Shortly after working the double dorsal finned fish boat side to Capt. Bo for the hook release, shark happily swims away for the next angler.

Client Action

After 2 days of successful pre-fishing, our clients were in for a treat – Cobia, Permit, Jacks, Tarpon, Barracuda and Sharks! Capt. Bo and I picked them up from their hotel and we embarked on a 3 day fishing extravaganza! The Kansas natives were completely elated with the beautiful weather and a chance to unthaw from an epic snowstorm sweeping the middle of the United States. Our first stop would be the wreck 35 miles away, southwest the Marquesas Islands. In the first 5 minutes, the son hooked a 40 lb cobia as his father watched in awe. It’s hard to imagine what went through his mind hooking a fish of such great magnitude on the same tackle they use to catch walleye or small mouth bass back home. It was non-stop action from there as they both doubled up on several occasions. If there were no cobia to be seen, we turned our attention to jacks, mutton snapper, and blue runners lurking within the depths. They were all easily enticed by a sinking jig slowly retrieved back to the boat with a twitching motion. The pelagic species that inhabit the wreck made for an abundance of variety and fun for these two northern anglers. The next species we targeted was the Bull shark. After warming up their forearms, we headed to another wreck to catch the falling tide. In less than 20 min, we had anchored, chummed and the 1st shark was on! I laughed as I watched the son’s eye’s bulge out of his head watching the line peel off the reel at extraordinary speed. 25 minutes (and many sweat drops) later, his fish was up to the boat where Capt. Bo quickly removed the hook and the son took a photo of a lifetime. Dad went next and as his fish took the bait, he leaped into the air, spinning! I knew it was not a bull shark, but a black tip shark– the most beautiful in my and Capt. Bo’s opinion.

After fishing the wrecks off shore, our clients had successfully caught cobia, jacks, blue runners, mutton snapper, bull and black tip sharks. The remainder of the fishing conquest would unfold on the flats. Our targets would include barracuda, permit and lemon sharks. At our first stop, we began trolling and suddenly I saw a tailing permit! A marvelous sight! These fish will cruise the shallow flats to forage for crabs and shrimp. Once they find a crab, it is breath taking to watch the V of a tail breach the surface. The client made a perfect cast, the fish ate, and 15 minutes later, he was taking a picture with a trophy of a lifetime, his first permit!! We continued trolling down the break where the trough and the bank met. Moments later, Capt Bo spotted 2 ‘cudas lurking in a pothole. I handed our clients the rods I had rigged with chartreuse ‘cuda tubes. They cast and began reeling in as fast as possible, ripping the tubes across the water’s surface. Both ‘cudas gave chase and one struck only 3 feet from the boat! The son’s jaw dropped as the ‘cuda hit like a freight train! Both father and son caught a couple ‘cudas each. With ample bait, we made our way further up the pristine flats to visually enhance the experience. As the tide fell harder and harder, the scent of the chum line drifted across the flat and into the deeper trough where these predators lurk. In an hour, 15-20 different sharks had scented the chum trail and one by one, they found the bait. Only fishing the last 4 hours of the day for sharks, our clients ended with 7 fish hooked and 4 to the boat. The biggest was a 10 ½ foot Lemon shark!! All our finned friends were released unharmed.

Our father – son duo expressed their sincere gratitude for what they called the “BEST fishing trip they had ever been on”. Capt. Bo and I were equally grateful for the opportunity to put such big smiles on their faces. Since we video and photograph our clients’ adventures and provide them the footage, our Kansas clients made it home with a nice keepsake enabling them to relive their trip of a lifetime anytime they please.

And there ya have it ~ the BEST of Key West in FIVE days!

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Deidra is an avid outdoors enthusiast and spokesmodel for the industry. By sharing her adventures infused with passion for the woods and the water, she aspires to spread the motivation and inspiration garnered from experiences in the Great Outdoors. Follow her on Facebook

 Deidra is partners with Capt. Bo Johnson in owning and operating Tenacity Guide Service Trips are available in Southwest Florida and Key West. She helps with everything from running the boat, catching the bait, rigging the rods, to marketing. Clients choose among the following adventures = Sharkin’, Goliath Grouper Tug-o-War, The BEST of Key West, Backcountry ~ Fishin’ the Flats, Tarpon the Silver King, Backcountry Scenery, and Corporate Retreat at sea.

If you read her article and want to experience the ultimate in sight fishing, you owe it to yourself to take a trip to Southwest Florida and/or Key West. There is no other place where such a diverse amount of angling opportunities could confront you in one of the most beautiful estuaries and islands in the United States. So Deidra invites you to come wet a line in these pristine waters and lose yourself in a true angling adventure fishing everything from the lush grass flats of the backcountry to the offshore wrecks of the wide open sea.

For more information, go to or Facebook  Email Deidra to book your adventure!

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