Experience the best fishing charters in Key West with Cowboy Cowgirl Sportfishing. Our family-owned fleet has been taking guests offshore, reef, and shark fishing since 1965. Whether you’re after a private adventure or an affordable shared trip, our captains know where the fish are biting. Explore our boats and trip options below to start planning your Key West fishing adventure today.
For nearly 60 years, Cowboy Cowgirl Sportfishing has been the trusted name for fishing in Key West. Our family-owned fleet offers something for everyone — from private deep-sea and reef trips to shared and shark fishing charters. Each boat is captained by seasoned locals who know these waters inside and out, ensuring every trip is safe, comfortable, and action-packed. Whether you’re looking for a luxury offshore experience, an affordable shared adventure, or a family-friendly day on the water, our team will help you make memories that last a lifetime.
Every vessel in our fleet is equipped for serious fishing and real comfort. The larger boats like the Cowgirl, Irish Cowboy, and Sanctuary feature air-conditioned cabins, restrooms, and shaded decks — perfect for longer offshore trips or multi-generational groups. The Blue Cowboy, Cowboy, and Knotty Cowgirl are versatile light-tackle boats ideal for inshore fishing, reef trips, and sandbar combos.
The Blue Cowboy also offers a unique historical fishing tour to the Marquesas Keys — a one-of-a-kind adventure that blends light tackle fishing with stories and sights from one of Key West’s most fascinating island chains.
No matter which you choose, you’ll enjoy professional gear, clean boats, and a crew that treats every charter like family.
Thinking about which trip or boat fits you best? Check out the options above, visit our blog for local fishing tips, or give us a call to plan the perfect day on the water.
Our boats depart daily from Historic Charter Boat Row in Key West — just minutes from downtown, the cruise docks, and major hotels. You’ll be fishing blue water within minutes, with the reef, wrecks, and Gulf Stream right at our doorstep. Guests love how fast we get to the action and how effortless the day feels from start to finish.
Depending on the season, our guests reel in mahi-mahi, tuna, sailfish, wahoo, grouper, snapper, and more — plus the thrill of shark fishing for species like bull, lemon, and hammerhead. Our captains adjust each trip to target what’s biting best, giving you the best shot at trophy catches and great eating fish. No two days are ever the same, and that’s what keeps anglers coming back year after year.
Which boat is best for families or beginners?
Our larger vessels like the Cowgirl and Sanctuary are great for families thanks to their roomy layouts, shade, and air conditioning. The crews are experienced with kids and first-timers, ensuring everyone has fun and catches fish.
Do you offer both private and shared fishing charters?
Yes, we offer both. Private charters are booked per boat for your group only, while shared charters pair small groups together for a more affordable trip without sacrificing quality.
Can we go shark fishing on any boat?
Absolutely! But mostly the Cowboy for the shorter inshore/reef trips, Shark fishing trips are among our most popular adventures, and our captains can arrange them on several boats depending on group size and conditions.
Do the boats have restrooms or air conditioning?
Several of our boats, including the Cowgirl, Irish Cowboy, and Sanctuary, Cowboy & Knotty Cowgirl are equipped with both A/C and restrooms for extra comfort.
What kinds of fish can we expect to catch?
Depending on the season and type of trip, you might catch mahi-mahi, wahoo, tuna, grouper, sailfish, snapper, or even a powerful shark. Our captains will recommend the best option for what’s biting when you visit.
Where do your trips depart from?
Most of our charters leave from Historic Charter Boat Row at 1801 N Roosevelt Blvd in Key West, conveniently located near downtown and popular hotels.
No matter which boat you choose, you’ll experience the same level of professionalism, local knowledge, and family hospitality that’s made Cowboy Cowgirl Sportfishing one of the most trusted names in Key West since 1965. Learn more about each boat above or explore our blog for insider stories, fishing reports, and seasonal tips to help you plan your perfect Florida Keys adventure.