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4 hours
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Get ready for an exhilarating adventure on the vibrant waters of Key West with our private deep sea fishing charters. Led by the skilled and experienced Captain, our team is dedicated to making your fishing trip unforgettable. Reel in the fight of a lifetime as you battle magnificent mahi, king mackerel, sailfish, and more. Our knowledgeable captain and mate will guide you to the sharky hotspots and employ various techniques, including trolling and bottom fishing, to maximize your chances of landing a trophy catch.
We believe in providing personalized service. Whether you're a seasoned angler or a curious first-timer, we'll tailor the experience to your skill level and preferences. We offer well-equipped vessels, clean facilities, and essential safety gear for a smooth journey
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Not recommended for travelers with spinal injuries
Suitable for all physical fitness levels
Offshore Fishing in Key West (Private Charter): • You will enjoy a private deep sea fishing charter in the waters of Key West. • We will board a well-equipped sportfishing vessel and venture out to prime fishing spots guided by experienced Captain and crew. • You will have the opportunity to reel in a variety of fish species, including mahi, king mackerel, sailfish, and more, while taking in stunning views of the ocean. Note: The duration of the charter will be 4 hours.
Duration: 4 hours Boat
Use of all tackle
Fishing Permits
Bait
Gratuity for Crew
Fuel Surcharge $150 due at the boat
For a full refund, cancel at least 24 hours before the scheduled departure time.
11 reviews
Total reviews and rating from Viator & Tripadvisor
IsraelP297,Jun 20, 2026
- Review from Tripadvisor
The Cowboy is one of the oldest most experienced fishing charter boats in Key West. Crew was very knowledgeable and experienced. Even though it was not a very good day for fishing, they made the experience much better. Went out of their way to try to find good fishing spots. Would highly recommend for groups of six or less. Four people being the better.

tjw953,Apr 5, 2026
- Review from Tripadvisor
Had an awesome time fishing with Sam and Caleb. Caught a large black fin tuna right off the bat, then taught to focus on sailfish. Had 2 get off but finally got one to connect and the fight was on. Sam and Caleb worked hard to get him finally caught and then Released. He ended up being over 7 feet and we got some awesome video of it tail walking and skimming the waves. Was an excellent experience. We highly recommend this charter, and we will return.

byungl2025,Jun 21, 2025
- Review from Tripadvisor
Caught some Mahi! Captain Chris and Daniel was the best! Knew the best spots and caught tons of fish! The boat was clean and ready to go as soon as we got there.
John R,Mar 11, 2025
- Review from Viator
We fished with Captain Bobby and Mate Chase on 3/8 and 3/9. Awesome guys to fish with and made sure to put us on fish. Caught well over 100 Yellowtails, 38 keepers on Saturday and went back Sunday and trolled for Tunas. Picked up a couple of nice Blackfins and i managed to loose another. Will definitely be coming back to fish with these guys again.
philipcU4546YL,Feb 12, 2025
- Review from Tripadvisor
It was a great day on the water. The Captain Hans and mate Adam were knowledgeable, courteous and professional. We caught some mackerel and Corbia. The corbia were strong fish and challenging to bring in. We had a blast. I would recommend the trip.
R6787RRkevinc,Feb 6, 2025
- Review from Tripadvisor
We had a great time with Cole & Adam ! Super knowledgeable about everything fishing here! Our first time sport fishing, we will be back. We hope to bring a group back for another venture. Highly recommend this outfit!
dougsZ6078OP,Jan 27, 2025
- Review from Tripadvisor
Captain Hans was excellent!! My bestie David had an awesome time. We highly recommend Cowboy Cowgirl charters for your next fishing trip !!!
Jeffrey R,Jan 26, 2025
- Review from Tripadvisor
This was a fishing trip of a lifetime, Captain and mates were 100% there to help and assist me when catching my fish. If I ever get another chance to go deep Sea fishing I will be calling these people. Thank You for such a wonderful trip.
V1274DIdaniela,Jan 8, 2025
- Review from Tripadvisor
My son and I had a great time on the four hour tour! We caught three fish between us, including a 35 inch barracuda! Thanks to the entire team for a wonderful memory.

S435NVjima,Aug 18, 2024
- Review from Tripadvisor
Another item off the #bucketlist ✅ Thanks to Cowboy Cowgirl SportFishing Charters for the awesome trip 👏 They filleted our Mahi on the dock and the restaurant at that Marina cooked out fish. Wow. Did it taste so good. And it doesn’t get any fresher than that. Amazing 🤩 #keywest #25thanniversary #mahi #bonitos #barracudas
















Operated by Cowboy Cowgirl Sportfishing Charters