Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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!
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!
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Anglers' gallery (424)
What anglers say
Reviews (459)
Daniel ElseRepeat angler5.0VerifiedNewone of my target species achieved!
3/4 Day Trip – Shared on October 28, 2026 • 1 adultthere was three of us on the trip which may it more enjoyable. all three of us caught. one giy had a 50lb sail fish and a 25 lb barracude. anither giy had a smaller barracuda and i jad a 12/13lb mahi mahi and a lottle tunny. we lost quote a few first off in the trip. butcthe captian kept going to to locate them and even kept is iut an hour longer than plannned to try and get a couple more after dark. would 100% book again and would advise anykne to book with them if in key west. 5 ⭐️ recommend all day long!
Georgina Simonson5.0Verified10/10 recommend!
3/4 Day Trip – Shared on August 22, 2026 • 2 adultsI just went on a charter with CowboyCowgirl this weekend, and my best friend and I had an awesome time. We were out for 6-8 hours and the captain and first mate made sure all of it was a blast. They were clearly skilled fishermen and boaters, and did everything they could to make sure each of us caught big fish, all while having a great day on the water. Captain Sam Woody and first mate Tyson made it happen!! Couldn't recommend this charter and group more!! Would absolutely do it again.
Thomas Wondrock5.0VerifiedAmazing time
Full Day Trip – Shared Charter on June 6, 2026 • 2 adultsThe crew worked increasingly hard to get us on fish and keep us on the fish. Dj was our first mate and this man never stopped moving. Hardest working first mate I have ever seen. We caught plenty of fish. Everyone had a great time. They even let is have the scraps so we could feed the massive tarpon by hand which was also a ton of fun. Thanks guys.
Merijn Leusink5.0VerifiedBest trip ever: Catched the maximum limit
Full Day Trip – Shared Charter on September 14, 2026 • 1 adultWe went with 4 person on a 8 hour trip with Caleb and the captain. Caleb worked hard on different strategies with succes: We catched 20 Mahi (boat limit!), 2 tuna and 1 tripletail. The Cowboy or Cowgirl is the best in the Keys
Chris Belcher4.7VerifiedAwesome Captain and crew of the Cowgirl!
Full Day Trip – Shared Charter on July 1, 2026 • 2 adultsCaptain Hans worked hard to find the fish, and then got us on them and kept us on them. The two mates Caleb and T (forgot his name) worked their butts off the entire trip, were well qualified, and you could tell they loved what they do. Couldn't have asked for a better pair of mates 11/10. Caught plenty of Mahi, and had an absolute blast!
Joe SchoonoverRepeat angler5.0VerifiedCaptain Nels put us on the fish! Great trip!
3/4 Day Trip – Shared on July 23, 2026 • 1 adultLoaded the boat with Mahi. Great captain and crew! For a short notice, walk on charter, the crew put in 100% effort to get us on the fish. Next time Inam in Key West I will definitely book another trip with these guys.
Liz W5.0VerifiedKnowledgeable & Personable
1/2 Day Trip – Private Charter - 1:00 PM on December 12, 2025 • 2 adultsCapt. Hans and first mate Caleb are a dynamic team! Friendly, very skilled, knowledgeable, take all precautions seriously, and excellent teachers. We caught trophy fish (barracudas) and some tasty yellowtail snapper (upon our request). Definitely will be scheduling a charter again with them 😊
Haley Robinson5.0VerifiedGreat experience
3/4 Day Trip – Shared on August 21, 2026 • 2 adultsLoved them! Most relaxing day in the sun and caught some Maui Maui which is what I was hoping for
Cane Hulsey4.7VerifiedGreat day of fishing!!
3/4 Day Trip – Shared on July 20, 2026 • 1 adultHad a great and successful day fishing. The crew knew where to go to catch them and all the way to cleaning them and sending us to a great place that prepared the fresh catch for us
Brett Gerhart5.0VerifiedPerfect first trip
Half Day Trip – Shared Charter on June 18, 2026 • 1 adultHad a great group on my boat! Capt. Chris and 1st Mate Talon were excellent.
FAQs about Cowboy Cowgirl 36 Ft Hatteras--Since 1965
- US $230 per person - Half Day Trip – Shared Charter (4 hours)
- US $230 per person - Half Day Trip – Shared Charter - 1:00 PM (4 hours)
- US $290 per person - 3/4 Day Trip – Shared (6 hours)
- US $290 per person - 3/4 Day Trip – Shared - 1:00 PM (6 hours)
- US $350 per person - Full Day Trip – Shared Charter (8 hours)
- US $650 per group - Inshore Shark Trip (3 hrs) (3 hours)
- US $650 per group - Inshore Shark Trip (3 hrs) - 2:00 PM (3 hours)
- US $650 per group - Inshore Shark Trip (3 hrs) - 4:00 PM (3 hours)
- US $1,000 per group - 1/2 Day Trip – Private Charter (4 hours)
- US $1,000 per group - 1/2 Day Trip – Private Charter - 1:00 PM (4 hours)
- US $1,000 per group - Sunset Tuna Trip 4 hrs (4 hours)
- US $1,500 per group - Full Day Trip – Private Charter (8 hours)
- US $1,700 per group - 10 HR Day Trip – Private Charter (10 hours)
- US $1,900 per group - 12 HR Day Trip – Private Charter (12 hours)
- US $2,500 per group - 12 HR Trip – Private Swordfishing (12 hours)
- Toilet We provide an enclosed bathroom on board for your privacy and comfort
- Fighting chair
- GPS
- Fishfinder
- Flybridge
- Live bait well
- Outriggers
- Ice box coolers with ice
- Rods, reels & tackle
- Live bait (When available!)
- Lures
- Catch cleaning & filleting (We don't charge extra for cleaning or filleting your catch—it's part of the mate's job. A customary 20% tip is appreciated to recognize their hard work)
- First mate (A skilled first mate is always on board to assist with all aspects of your trip. A 20% tip is customary and appreciated to recognize the crew's hard work and dedication)
- Fishing license (All necessary fishing licenses are included in the price, so you're fully covered and ready to fish)
- Inshore fishing
- Nearshore fishing
- Offshore fishing (How far we go offshore depends on the trip length: half-day trips stay closer to shore, 3/4-day trips go a bit farther, and full-day trips venture deeper for bigger catches. Our inshore shark trips stay near the coastline)
- Reef fishing
- Wreck fishing
- Light tackle
- Heavy tackle
- Bottom fishing
- Trolling
- Spinning
- Jigging
- Kite fishing
- Deep sea fishing
- Amberjack
- Barracuda (Great)
- Dolphin (Mahi Mahi)
- Marlin (Blue)
- Sailfish
- Shark (Blacktip)
- Shark (Bull)
- Shark (Hammerhead)
- Snapper (Mutton)
- Swordfish
- Tuna (Blackfin)
- Wahoo
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Amberjack
Barracuda (Great)
Dolphin (Mahi Mahi)
Marlin (Blue)
Sailfish
Shark (Blacktip)
Shark (Bull)
Snapper (Mutton)
Swordfish
Tuna (Blackfin)
WahooCompare similar fishing charters
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