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Explore Your Ultimate Key West Fishing Adventure

Choose Your Perfect Experience From Over 33 Unforgettable Trip!

**Shared/Group**Exclusive Private Charters**Shark Adventures-Thrill Seeker?

Best Key West Fishing Charters

Discover the Best Key West Fishing Charters for Every Adventure

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.

Why Anglers Choose Cowboy Cowgirl Sportfishing:

  • 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

QUALITY BOATS FOR YOUR FISHING CHARTERS IN KEY WEST!