Captain of Cowboy Charters has been guiding people to fish in the Florida Keys. These waters are famous worldwide for their unusually diverse game fishery, and with two fully equipped Hatteras boats at his disposal, he has an offshore fishing trip to suit every type of angler.
Cowboy is the smaller of the company’s 6 boats. A well-appointed 36' Hatteras sportfishing yacht, vessel makes for a comfortable ride for groups of up to six people plus the crew. The boat features a head, as well as outriggers, downriggers, and a fighting chair for a professional and comfortable fishing experience. With a large deck area, everyone will be able to get involved in the offshore action.
The captain is well known for his ability to put his guests on fish, whatever their prior experience. He and his first mate will guide you across the offshore waters, providing all the know-how and equipment you need to catch species such as Mahi Mahi, Sailfish, Marlin, Wahoo, and many more. Cowboy and Cowgirl Charters’ trips usually involve a combination of trolling and bottom fishing, and you may be able to try kite fishing for Sailfish and other exciting pelagic fish when conditions allow.
Want to make your trip extra special? Click on the charter operator’s bio below and check out Cowboy’s bigger – and even more luxurious – sister. You won’t regret it!
Rating summary
Photos & videos by reviewers (312)
Angler rating
Anglers claimed
Good experience
87%
Appropriate for children
82%
Friendly captain
97%
Satisfied with the boat
92%
Recommend this charter
88%
Caught fish
77%
Aug 7, 2025
3/4 Day Trip – Shared Charter (AM)
The captain was breaking in a new mate which can often be problematic, however Chris and Paul worked very well together right from the start and both were vey friendly and knowledgeable. Caught some nice Mahis and Bonitas, along with few small jacks. Great time with a crew that worked hard to ensure everyone was catching fish.
The captain was breaking in a new mate which can often be problematic, however Chris and Paul worked very well together right...
May 31, 2025
3/4 Day Trip – Shared Charter (AM)
Had a wonderful day with Paul and Kris! Would book this trip again. There were many other boats out there so we knew catching fish would be slim but we did catch Cero, Bonita and Mahi. Paul then took us to a spot for more action on yellow fin. We took our catch over to Mac's for them to cook, be sure to ask for Jasmine she's wonderful. Our fresh fish was so delicious. If you haven't experienced having your fish cooked for you right after your trip, you definitely need to do this!
Had a wonderful day with Paul and Kris! Would book this trip again. There were many other boats out there so we knew catching...
Jul 5, 2025
3/4 Day Trip – Shared (PM)
Had a really great experience here guys. I was a single slot on the trip with another group of 🐠Fishing on the boat. The deck Hand Daniel did an amazing job and definitely brought great vibes and everyone had a really fun time and captain Hans was a real joy to speak with. He had lots of experience and played some really great music I enjoyed. Just book it with these guys don’t think twice.
Had a really great experience here guys. I was a single slot on the trip with another group of 🐠Fishing on the boat. The deck...
May 25, 2025
3/4 Day Trip – Shared Charter (AM)
The captain and crew are awesome, the boat is clean and relatively comfortable. If you don’t mind leaning on the rail a bit. Great choice if you were looking for something more affordable without renting the whole boat, but still with the private charter experience. The boat definitely feels like a private experience while you were on it which really benefits when fishing for anything offshore.
The captain and crew are awesome, the boat is clean and relatively comfortable. If you don’t mind leaning on the rail a bit. Great...
Aug 12, 2025
3/4 Day Trip – Shared Charter (AM)
Capt John and his First Mate Austin were great. Very friendly and Professional and knew the spots to catch. They both made sure everyone on board was good during the fishing expedition. Highly Recommend. A+++++++
Capt John and his First Mate Austin were great. Very friendly and Professional and knew the spots to catch. They both made sure...
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Rating summary
Photos & videos by reviewers (312)
Angler rating
Anglers claimed
Good experience
87%
Appropriate for children
82%
Friendly captain
97%
Satisfied with the boat
92%
Recommend this charter
88%
Caught fish
77%
Experience:
Boat
Crew
Overall
3/4 Day Trip – Shared Charter (AM) on August 7, 2025
The captain was breaking in a new mate which can often be problematic, however Chris and Paul worked very well together right from the start and both were vey friendly and knowledgeable. Caught some nice Mahis and Bonitas, along with few small jacks. Great time with a crew that worked hard to ensure everyone was catching fish.
The captain was breaking in a new mate which can often be problematic, however Chris and Paul worked very well together right from the start and both were vey friendly and knowledgeable. Caught some nice Mahis and Bonitas, along with few small jacks. Great time with a crew that worked hard to ensure everyone was catching fish.
Experience:
Boat
Crew
Overall
3/4 Day Trip – Shared Charter (AM) on May 31, 2025
Had a wonderful day with Paul and Kris! Would book this trip again. There were many other boats out there so we knew catching fish would be slim but we did catch Cero, Bonita and Mahi. Paul then took us to a spot for more action on yellow fin. We took our catch over to Mac's for them to cook, be sure to ask for Jasmine she's wonderful. Our fresh fish was so delicious. If you haven't experienced having your fish cooked for you right after your trip, you definitely need to do this!
Had a wonderful day with Paul and Kris! Would book this trip again. There were many other boats out there so we knew catching fish would be slim but we did catch Cero, Bonita and Mahi. Paul then took us to a spot for more action on yellow fin. We took our catch over to Mac's for them to cook, be sure to ask for Jasmine she's wonderful. Our fresh fish was so delicious. If you haven't experienced having your fish cooked for you right after your trip, you definitely need to do this!
Experience:
Boat
Crew
Overall
3/4 Day Trip – Shared (PM) on July 5, 2025
Had a really great experience here guys. I was a single slot on the trip with another group of 🐠Fishing on the boat. The deck Hand Daniel did an amazing job and definitely brought great vibes and everyone had a really fun time and captain Hans was a real joy to speak with. He had lots of experience and played some really great music I enjoyed. Just book it with these guys don’t think twice.
Had a really great experience here guys. I was a single slot on the trip with another group of 🐠Fishing on the boat. The deck Hand Daniel did an amazing job and definitely brought great vibes and everyone had a really fun time and captain Hans was a real joy to speak with. He had lots of experience and played some really great music I enjoyed. Just book it with these guys don’t think twice.
Experience:
Boat
Crew
Overall
3/4 Day Trip – Shared Charter (AM) on May 25, 2025
The captain and crew are awesome, the boat is clean and relatively comfortable. If you don’t mind leaning on the rail a bit. Great choice if you were looking for something more affordable without renting the whole boat, but still with the private charter experience. The boat definitely feels like a private experience while you were on it which really benefits when fishing for anything offshore.
The captain and crew are awesome, the boat is clean and relatively comfortable. If you don’t mind leaning on the rail a bit. Great choice if you were looking for something more affordable without renting the whole boat, but still with the private charter experience. The boat definitely feels like a private experience while you were on it which really benefits when fishing for anything offshore.
Experience:
Boat
Crew
Overall
3/4 Day Trip – Shared Charter (AM) on August 12, 2025
Capt John and his First Mate Austin were great. Very friendly and Professional and knew the spots to catch. They both made sure everyone on board was good during the fishing expedition. Highly Recommend. A+++++++
Capt John and his First Mate Austin were great. Very friendly and Professional and knew the spots to catch. They both made sure everyone on board was good during the fishing expedition. Highly Recommend. A+++++++