At Cowboy Cowgirl Sportfishing, we provide the best fishing charters in Key West. We combine years of experience with the largest and most flexible fleet in the Florida Keys. No matter if you want offshore fun, reef fishing, family time inshore, or exciting shark hunts — we have the right trip for you.
Our charters aren’t cookie-cutter. Each trip is designed for your group’s preferences. This could mean several things. You might go fishing for trophy sailfish in the ocean. You could also catch snappers on the reef. Another option is to combine fishing with a trip to a private sandbar for swimming and snorkeling.
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.
Each vessel is maintained to the highest standards, with modern tackle, safety gear, and comfortable amenities. Some boats have air-conditioned cabins for long days at sea. Others are made for speed and flexibility when fishing or exploring wrecks and reefs.
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.
Each vessel is maintained to the highest standards, with modern tackle, safety gear, and comfortable amenities. Some boats have air-conditioned cabins for long days at sea. Others are made for speed and flexibility when fishing or exploring wrecks and reefs.
Over 50 years of experience (est. Three generations of the Baumgarten family have built a strong reputation. They have made fishing a Key West tradition for visitors from all over the world.
Seven well-equipped boats for every type of trip. Choose from our 47-foot Hatteras Sanctuary, made for offshore luxury. Or pick our nimble center consoles, which are great for inshore action. You can find the ride that best fits your fishing goals.
Family-friendly and group-friendly options We specialize in trips where kids, parents, and even grandparents can all fish together safely and comfortably. Large groups—like bachelor parties or corporate outings—also find our fleet ideal for hosting everyone at once.
Private and shared charters available Private trips are fully customizable, while shared charters give smaller groups an affordable way to experience deep sea fishing in Key West without booking an entire boat.
Trusted by thousands of returning guests each year Many of our anglers come back year after year, often requesting the same captain by name. Our reviews highlight not just great catches but also the friendly, professional service that keeps families and fishing buddies coming back.