BEST FISHING CHARTERS IN KEY WEST-PRIVATE, SHARED & SHARK TRIPS SINCE 1965
Explore Our Key West Fishing Experiences
Whether you’re booking your first fishing trip or you’ve spent years on the water, Cowboy Cowgirl Sportfishing offers a variety of charters to match your style of adventure. Our captains run daily offshore, reef, wreck, and shark fishing trips, giving you plenty of options for an unforgettable day on the water.
Offshore / Deep Sea Fishing
Head beyond the reef in search of mahi-mahi, tuna, wahoo, and sailfish. Our captains know exactly where the fish are moving and tailor each trip to the day’s conditions.
Reef & Wreck Fishing
A great choice for families and beginners, these trips offer steady action for snapper, grouper, jacks, mackerel, and more—all in calmer waters.
Shark Fishing
Experience the excitement of battling bull sharks, lemons, blacktips, and other powerful species on dedicated shark trips available inshore, at the reef, or offshore.
No matter which trip you choose, our team is here to deliver a fun, safe, and memorable fishing experience in the waters of Key West.
Personalized Fishing Adventures for Every Skill Level
Every trip with Cowboy Cowgirl Sportfishing is tailored to the goals and experience level of your group. Whether you’re brand new to fishing or a seasoned angler, our captains take the time to understand what you want to catch and how you prefer to fish.
Expert Guidance From Local Captains
Our captains and mates provide hands-on instruction, local knowledge, and proven techniques to help you get the most out of your time on the water. From choosing the right bait to coaching you through the bite, you’re supported every step of the way.
Modern Boats & Quality Gear
Each boat in our fleet is equipped with reliable tackle, clean and comfortable layouts, and advanced fish-finding electronics. We use gear that’s built for offshore, reef, wreck, and shark fishing success.
Your Safety Comes First
All vessels meet U.S. Coast Guard safety standards and are maintained year-round. Your captain monitors weather, sea conditions, and safety protocols to ensure every trip is enjoyable and worry-free.
Let our family create the perfect fishing experience for yours. Book your adventure today and discover why anglers have trusted our charter fleet since 1965.
