Experience legendary sportfishing in Key West with Cowboy Cowgirl SportFishing Charters. Our fleet of offshore charter boats offers deep sea fishing in Key West, shark fishing, and private fishing trips in the Florida Keys.
Compare boats, trip lengths, and rates on our Key West Fishing Charters page.
Pick the kind of trip that fits your group. We'll help you match it to the right boat afterward.
Starting at $200 per person
For solo anglers, couples and small groups who want an affordable day of fishing without booking a whole boat.
See Trips
Starting at $850 per boat
Reserve the entire boat for your group. Pick your trip length and fish the way you want to fish.
See Trips
Starting at $600 per trip
Inshore, reef and deepwater shark trips. Heavy tackle, big fish, catch and release.
See Trips
Light tackle fishing, Marquesas Keys runs, snorkel-and-fish combos and other specialty trips.
See TripsNot sure which trip is right for you? Call or text us at (305) 304-2946 and we'll help match your group with the right boat and trip.
Listed charter price excludes applicable fuel surcharge and crew gratuity.
Pick the experience that fits your group. Each page covers seasons, target species, and pricing in detail.
Steady action in calmer water over reefs and historic wrecks.
Heavy tackle, big predators, and ethical catch-and-release.
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
The 45' Cowgirl is a classic Hatteras built for serious Key West offshore fishing with added comfort for longer days on the water. She offers a spacious layout, air conditioning, and plenty of room for families and groups of up to six guests.
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.
Three Generations. One Family. These Waters Are Home.
Cowboy Cowgirl SportFishing Charters began in Key West in 1965 and has grown into a three-generation family fishing operation. What started with founder Hans Baumgarten and the original Cowboy continues today with the Baumgarten family taking anglers onto the same Key West waters they have fished for decades.
Our captains are U.S. Coast Guard licensed locals, and our fleet gives us the right boat for families, first-timers, and serious anglers alike.
Up to 6 guests per boat. Beginners welcome — the crew handles the rest.
Listed charter price excludes applicable fuel surcharge and crew gratuity.
Great for
Bringing kids? Start with a family-friendly fishing charter.
Key West offers fishing opportunities throughout the year, with different species and techniques changing by season.
