Budget-Friendly Charters for Solo/Splits, Plus Over 30+ Private Custom Charter Options-Click Here
**Shared/Group**Exclusive Private Charters**Shark Adventures-Thrill Seeker?
At Cowboy Cowgirl Sportfishing, we offer the best fishing charters in Key West, combining decades of experience with the largest and most versatile fleet in the Florida Keys. Whether you’re after offshore excitement, reef fishing action, inshore family fun, or thrilling shark hunts — we have the perfect trip for you.
With seven boats in our fleet, we cater to every kind of angler — from hardcore sportfishing pros to families with kids. Our captains are seasoned locals who know the waters inside and out. Whether you’re booking a private deep sea adventure or a shared fishing charter, you’re in expert hands.
Looking for the best Key West fishing charter for your group? Browse the options below to choose by boat, trip type, or fishing style. You can book directly online or reach out to our team for help customizing the perfect experience. All our trips include fishing licenses, bait, tackle, and expert guides to help you reel in your next big story.
Over 50 years of experience (est. 1965)
Seven well-equipped boats for every trip type
Family-friendly and group-friendly options
Private and shared charters available
Trusted by thousands of returning guests each year
Enjoy affordable shared (group-split-makeup) fishing charters in Key West. Come catch some Mahi, Wahoo, Black Fin tuna, Sailfish, and Marlin! Offshore Deep Sea Fishing with our knowledgeable and professional crew!
Learn MoreReady for an affordable private Key West shark fishing charter? Join Key West Shark Hunters for a safe, catch‑and‑release adventure targeting bull, hammerhead, and lemon sharks and more, in calm, clear waters.
Learn MoreBlue Cowboy is a luxury 34′ Contender, designed for high-end Marquesas Key historical tours and world-class fishing. Combining speed, comfort, and top-tier equipment, it offers an exclusive experience for those seeking adventure in the pristine waters beyond Key West.r.
Learn MoreExperience a private fishing adventure aboard our 36-foot Hatteras, perfect for up to six guests. Enjoy a fully equipped boat with top-notch amenities, expert crew, and action-packed fishing in the waters of Key West!
Learn MoreUnique to this vessel is our local trip option, which combines exhilarating fishing experiences with leisurely time at a picturesque sandbar.
Learn MoreExperience the Excitement of Inshore, Light Tackle or Shark Fishing Aboard the Cowgirl II in Key West!
Learn MoreRelax on the flybridge with wide, comfortable seating and take in ocean views as you plan your next big catch.Equipped with tournament-grade tackle, the “40 ft is ready to make your fishing ambitions a reality.
Learn MoreThe “Cowgirl” provides a great adventure. You can fight big sea monsters or enjoy a relaxing day of reef fishing. It has all the comforts of home.
Learn MoreThe 47 ft Sanctuary offers private offshore, deep sea, reef, wreck, and shark fishing in Key West—delivering tournament-level performance with air-conditioned comfort and expert crew.
Learn MoreExperience premier night snapper/grouper fishing in Key West on this private 5-hour trip aboard our 45’ Hatteras, Cowgirl. Departing at 5 PM, you’ll target snapper and grouper during the prime evening bite — perfect for up to 6 guests looking to beat the heat and hook into big fish under the stars
Learn MoreGive them an experience they’ll remember!
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