Experience legendary sportfishing in Key West with Cowboy Cowgirl Sportfishing. Our fleet of offshore charter boats offers deep sea fishing, shark fishing, and private fishing trips in the Florida Keys.
Key West sits at the southern tip of Florida, where the Gulf of Mexico meets the Atlantic Ocean. This unique location creates some of the best fishing in the United States. Warm currents bring big fish close to shore year-round. From mahi-mahi and sailfish in the deep blue water to snapper and grouper on local reefs, the variety is hard to match anywhere else.
Cowboy Cowgirl Sportfishing has called Key West home since 1965. We are a family-owned business with three generations of fishing knowledge. Our captains grew up on these waters. They know where the fish are, what they bite on, and how to get you on them fast. That kind of local experience makes a real difference on the water.
We run six boats from two Key West marinas. Whether you want a half-day trip or a full-day adventure, we have options that fit your schedule and budget. Unlike simple boat rentals in Key West, our fleet includes tournament-tested sportfishing vessels with top-of-the-line gear. Every Key West boat in our fleet comes with a professional captain, equipment, bait, tackle, and fishing licenses included.
Beginners are always welcome. Our crew will teach you everything from casting to reeling in your first catch. Experienced anglers will appreciate our focus on finding quality fish and putting you in the best position to land them. We offer private charters for groups who want the boat to themselves and shared trips starting at just $200 per person for those looking for an affordable way to fish Key West. For those seeking an adrenaline rush, our Key West shark fishing charters are among the most exciting trips we run.
Safety is our top priority. All captains are U.S. Coast Guard licensed with years of experience. Our boats are well-maintained and equipped with modern navigation and safety gear. We check weather conditions before and during every trip to make sure you have a safe, enjoyable day on the water. For a detailed breakdown of what different trips cost, see our guide to Key West fishing charter prices.
Private, shared, and shark fishing trips since 1965. Choose from our tournament-tested fleet of sportfishing vessels.
Six Tournament-Ready Vessels • Expert Local Captains • All Skill Levels Welcome
Per Person (4-Hour Trip)
Affordable small-group deep-sea fishing in Key West—expert captains, great catches, and nonstop fun! Join up to six anglers for a budget-friendly experience.
4-Hour Charter, up to 6 people
Step aboard the 36' Cowboy, a classic Hatteras sportfishing boat offering comfortable offshore fishing trips, shark fishing adventures, and shared fishing charters in Key West.
4-Hour Charter, up to 6 people
The 40' Irish Cowboy is a spacious Luhrs sportfishing yacht built for anglers who want a smooth, comfortable ride offshore. With a fully air-conditioned cabin, plenty of space, and the power to reach productive offshore waters, this boat is ideal for families, small groups, and anyone looking to enjoy a premium Key West fishing charter experience without sacrificing comfort.
4-Hour Charter, up to 6 people
Classic 45' Hatteras Built for Offshore Fishing Adventures
4-Hour Charter, up to 6 people
The best offshore fishing charter in Key West. 47' Hatteras with A/C comfort, tournament-winning crew, and proven offshore results since 1965.
4-Hour Charter, up to 6 people
Ultimate light tackle comfort with shade and speed combined. A high-performance fishing machine for stand-up fishing enthusiasts who love hands-on action.
4-Hour Charter, up to 6 people
Where light tackle fishing meets the remote Marquesas Keys. A premium private charter with the range and stability to reach backcountry areas most boats can't.
Looking for something different? Try our shark fishing, night snapper, or historical Marquesas adventures.
3-Hour Inshore Trip, up to 6 people
Test your strength with the ultimate thrill — Key West shark fishing charters. Go head-to-head with bull sharks, hammerheads, and blacktips. Trusted local experts since 1965.
4-Hour Charter, up to 6 people
Night snapper fishing done right — grouper and good times every night. Beat the heat, skip the crowds, and hook serious fish when the sun goes down.
Half Day Charter, up to 6 people
Explore the remote Marquesas Keys — a pristine natural atoll 30 miles west of Key West. Light tackle fishing meets remote exploration aboard the premium 34' Blue Cowboy.
From deep sea adventures to calm reef fishing, our expert captains deliver unforgettable trips for every type of angler.
Perfect for families and beginners seeking steady action in calmer waters. Drop lines over historic shipwrecks and reefs teeming with yellowtail, snapper, grouper, and jacks.
Test your strength against bull sharks, hammerheads, blacktips, and more. We offer inshore, reef, and offshore shark trips with ethical catch-and-release practices.