Cowboy Charters – Blue Cowboy
There's no place like Key West to fulfill your fishing dreams and if you're looking for a company to lead the charge, Cowboy Charters is at your service! Captain Daniel Hawkins and his skilled crew know the ways of the fish and are happy to share the knowledge with their customers.
It will all start on a comfortable 34' Contender with plenty of space to sit up to 6 adventurous anglers and twin 300 HP Yamaha engines. The vessel is rigged with the top-notch navigational equipment to keep you on your prey and a live bait well. If you're going on a longer expedition, there's a private porta potty on board, so you can fish without a worry in the world.
But the top-of-the-line boat is only one of many perks Cowboy Charters has to offer. The professional crew makes it their mission to put you on the bite. Chase Billfish superstars like White Marlin and Sailfish, or land sizeable Mahi Mahi, Mutton Snapper, and Amberjack. If your thrill is chasing apex predators, targeting Sharks is another specialty of Capt. Daniel. The waters around Key West are as plentiful as they are varied.
Feel free to come fishing with your kids, all ages are welcome aboard. The crew will have safety jackets for everyone. You'll find all the fishing gear you need on the boat, including reliable Venspaal and Penn spinning rods. At the end of the day, you will get your catch cleaned and filleted for your convenience.
Everything will be provided for your next fishing escapade, just remember to bring your favorite food and drinks for the trip, and leave everything else in the capable hands of Cowboy Charters! New fishing horizons await!
There's no place like Key West to fulfill your fishing dreams and if you're looking for a company to lead the charge, Cowboy Charters is at your service! Captain Daniel Hawkins and his skilled crew know the ways of the fish and are happy to share the knowledge with their customers.
It will all start on a comfortable 34' Contender with plenty of space to sit up to 6 adventurous anglers and twin 300 HP Yamaha engines. The vessel is rigged with the top-notch navigational equipment to keep you on your prey and a live bait well. If you're going on a longer expedition, there's a private porta potty on board, so you can fish without a worry in the world.
But the top-of-the-line boat is only one of many perks Cowboy Charters has to offer. The professional crew makes it their mission to put you on the bite. Chase Billfish superstars like White Marlin and Sailfish, or land sizeable Mahi Mahi, Mutton Snapper, and Amberjack. If your thrill is chasing apex predators, targeting Sharks is another specialty of Capt. Daniel. The waters around Key West are as plentiful as they are varied.
Feel free to come fishing with your kids, all ages are welcome aboard. The crew will have safety jackets for everyone. You'll find all the fishing gear you need on the boat, including reliable Venspaal and Penn spinning rods. At the end of the day, you will get your catch cleaned and filleted for your convenience.
Everything will be provided for your next fishing escapade, just remember to bring your favorite food and drinks for the trip, and leave everything else in the capable hands of Cowboy Charters! New fishing horizons await!

| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
Had some sporty conditions, but Capt. Jake made it as comfortable as possible. Perfect boat outfitted for fishing in Key West and Jake put us on the meat. I am a current Captain myself of a yacht and Jake took great care of the guests I brought aboard the charter. First class guy and he knows the area well. Highly recommend!
Phil was an awesome captain with cowboy charters. Phil went above and beyond, he worked his butt off making sure we had as many lines out as possible and fresh bait. We caught about 12-15 dolphin. We did this as a last minute thing and it couldn't have been better decision! I highly recommend getting phil as your offshore charter guide
Stock Island, Florida, United States
Legendary Sportfishing in Key West – 60 Years Strong, Three Generations Deep! Step aboard one of our 6 premier fishing vessels, where 60 years of fishing excellence meets thrilling adventures in the world-renowned waters of Key West, FL. A family tradition spanning three generations, our fleet of six exceptional boats offers something for everyone – from seasoned anglers to families looking for an unforgettable day on the water. With a legacy of winning tournaments and creating lifelong memories, we specialize in offshore action for some of the most exciting species Key West has to offer. From bottom fishing to Offshore– our trips are all about chasing the big bites that make your heart race, whether it's the dazzling Mahi Mahi, powerful Tuna, sleek Wahoo, or acrobatic Sailfish. A Fleet Built for Adventure Whether you're looking for a luxurious offshore fishing experience or a shared group charter, our fleet is ready to deliver. Each boat is fully equipped with tournament-grade gear, spacious seating, and all the amenities you need for comfort and excitement on the water. From our iconic fleet, our vessels are helmed by captains with experience and unmatched knowledge of these legendary fishing grounds. Unmatched Expertise, Endless Thrills Fishing with our fleet isn't just a trip – it's a chance to learn from a team with generations of angling expertise. Our captains and crew know the waters of Key West like the back of their hand, and they're here to ensure you have the trip of a lifetime. Whether it's mastering trolling techniques, spotting fish, or simply enjoying the stunning views, we'll make sure you leave with incredible memories. What's Included: Top-tier equipment: Rods, reels, bait, tackle – we've got it covered. Family-friendly service: Trips suitable for anglers of all ages and experience levels. Catch care: Your captain will clean and fillet your catch for you. Comfort: Modern boats with shaded seating, clean restrooms, and plenty of space. Come fish with a team that's been making dreams come true for six decades. Cowboy Cowgirl Sportfishing Charters is more than a fishing trip – it's a slice of Key West history, filled with adventure, expertise, and passion. Book your trip today and discover why we're one of the most celebrated names in Key West fishing!

Capt Woody (Sam) W.
Captain

Capt Cole B.
Captain

Sharky (Mark) B.
Business partner

Capt Cuzzy (Chris) B.
Captain




You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
Pickup not included
Transfer to/from departure site is not included in trip rates.
When the captain confirms your trip, FishingBooker charges your credit card a 10% deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Cash
Visa
Mastercard
American Express
PayPal
Checks
Bank transfer
When paying the remaining balance with a credit card, an additional 3% charge will apply.
