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Cowboy Cowgirl Sportfishing

Fishing Charters in Key West, Florida

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Scroll Through our Fleet Key West Boat Charters

a man holding a fish in the water

Explore Our Diverse Fishing Charters:

  • Deep Sea Fishing
    Dive into the depths of Key West’s waters with our Deep Sea Fishing Adventures. Target a variety of big game species and feel the thrill of a challenging catch.
  • Family-Friendly Excursions
    Bring your family along for a fun and safe fishing experience. Learn more about our family-friendly charters at Cowboy Cowgirl Family Fishing.
  • Tournament Fishing
    Ready for competition? Join our tournament-level fishing expeditions and test your skills. Check out Cowboy Cowgirl Tournament Fishing for more details.
  • Luxury Fishing Experiences
    Indulge in a high-end fishing journey with top-notch amenities. Visit Cowboy Cowgirl Luxury Charters for an exclusive fishing experience.

Our Services - Tailored For Every Angler:

  • Personalized Charter Planning We work with you to customize your fishing trip, ensuring it matches your expectations and skill level.
  • Expert Guidance and Support Our skilled crew provides hands-on assistance and insights, making your fishing adventure both educational and enjoyable.
  • State-of-the-Art Equipment We equip you with the latest fishing gear and technology to enhance your chances of a great catch.
  • Safety as a PriorityYour safety is paramount. Our charters adhere to the highest safety standards, ensuring a secure and worry-free experience.
a group of people on a boat

The Best Charters in Key West!
★★★★★

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FISH ON!!!!

BEST fishing EVER!! I hesitate to give this review because once I do it will be even harder to get a reservation with this OUTSTANDING fishing charter.I have fished my entire life and taken many charters. I do not give reviews easily, but I just had to compliment the Cowboy Cowgirl Charters as one of the best charters I have ever been on. This Captain knows where the fish live and he takes you to them. He finds the fish, you just have to catch them and catch them we did! An amazing day on a very safe boat. You won't be disappointed if you charter with Cowboy Cowgirl Charters. BRAVO!!!!

– Melissa R, TripAdvisor
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Three Great Private Charters!

I booked three trips for clients. Capt AJ and mate Cole (two trips) and Capt Nels and mate Justin (one trip) were excellent. They made my guests feel welcome and at ease. They interacted with my guests in a positive and professional manner. Each of my guests had significant and quality time on the rods. They helped create great memories. While it was a primarily a fishing trip for my guests, it was still a business outing for me and the team made me look great. Many thanks to Michelle for coordinating lunches and additional beverages.

– lizzyrunsfar, TripAdvisor
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Key West Blast!

I had an amazing time on the deep sea fishing charter with Captain Chris and the crew! The team was incredibly knowledgeable and friendly. We caught a variety of fish, and the crew was very helpful in assisting and teaching us the best techniques. The atmosphere was fun and inclusive, perfect for both first-timers and seasoned anglers. Highly recommend this unforgettable experience!

– Carolina C, TripAdvisor
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Best Fishing Trip of My Life!

After many years, I decided to revisit my fishing experience with Cowboy Charters, and it was absolutely worth it! I caught my first Sailfish, along with some Bonitas, during a trip in March. The boat was comfortable, with refreshing AC, adding to the overall great experience. We saved the Bonitas for a tournament later in the month. Releasing the Sailfish back into the water was just as fulfilling. I Highly recommend Cowboy Charters for an unforgettable fishing adventure.

– Jeffrey R, TripAdvisor
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Amazing Offshore Fishing Trip!

We had an incredible experience with Cowboy Cowgirl Charters on our deep Sea fishing trip. Coming from the West Coast of Florida, we were eager to get out there deep sea fishing in this area again and we were not disappointed. The crew was knowledgeable, friendly, and made sure we had an unforgettable day on the water. We caught and released a beautiful sailfish and caught some nice Mahi for dinner and even was able to bring some home, which was the highlight of our trip. We can't wait to come back again! If we could give more than five stars, we would. Highly recommend Cowboy Cowgirl Charters for an amazing fishing adventure

– Brittany K, TripAdvisor