OUR PRIVATE CHARTER BOATS – CHOOSE YOUR KEY WEST FISHING ADVENTURE
Meet the Fleet – Private Charter Boats Built for Every Adventure
Each private charter boat in the Cowboy Cowgirl Sportfishing fleet is locally owned, professionally maintained, and captained by Key West pros who know these waters by heart. Whether you’re chasing offshore trophies, exploring the historic Marquesas Keys, or planning a relaxed family outing, we make it simple with easy online booking, real-time availability, and multiple payment options. Every trip is private and customized for your group—just as we’ve been doing since 1965.
The 34-foot Contender, The 34-foot Contender, Blue Cowboy, is a light-tackle specialist built for both performance and exploration. She’s the preferred boat for our Marquesas Key Historical Tour & Fishing Trip—a one-of-a-kind journey blending history, adventure, and incredible scenery. The Marquesas Islands hold over 200 years of stories: treasure hunting, smuggling, shipwrecks, bird sanctuaries, and record-breaking catches. With crystal-clear water averaging just 10–20 feet deep, it’s an unforgettable look at a part of Key West most people never see. These trips require a minimum of six to eight hours to explore fully.
The 37-foot Contender, Knotty Cowgirl, is our combo expert, perfect for snorkel + fish charters and sandbar getaways. Families love her versatility, smooth ride, and shaded comfort between reef stops.
The 36-foot Hatteras, Cowboy, is a Key West classic. Known for great catches, steady speed, and reliability, she’s one of the area’s most recognized sportfishing boats and a proven producer year after year.
Our 40-foot Luhrs, Irish Cowboy, balances comfort and capability. With cool A/C, shaded seating, and plenty of space, she’s perfect for families or corporate groups wanting an easy-going yet serious day of fishing.
The 45-foot Hatteras, Cowgirl, is a tournament-winning deep-sea boat that targets marlin, sailfish, tuna, and wahoo offshore. She delivers classic sportfishing performance with a friendly, hardworking crew and stellar reviews from happy anglers.
The 47-foot Hatteras, Sanctuary, offers a spacious, air-conditioned cabin and a comfortable, stable ride for longer offshore runs. Another tournament-proven vessel, she’s ideal for groups who want extra room to relax while chasing blue-water species.
Together, these boats form one of the most complete private charter fleets in the Florida Keys—ranging from fast center-consoles to seasoned offshore battlewagons. Cowboy Cowgirl Sportfishing is also home to Key West Shark Hunters, known for thrilling shark-fishing adventures targeting bull, lemon, and blacktip sharks for catch-and-release excitement.
No matter which boat you choose, you’ll fish with captains who love sharing the real Key West—clean boats, quality gear, and decades of experience on the water. Before departure, grab performance shirts, buffs, and hats from our BiteBackBrand Local Legends line at the dock to stay cool and protected while looking like part of the crew.
Ready to Book Your Private Charter?
All of our private fishing charters can be booked instantly online with secure payment options, or you can call 305-304-2946 to talk directly with our dock team. We’ll help you match the right boat, trip length, and fishing style for your group—and get you on the water for a Key West fishing adventure you’ll never forget.