Charter Operator
Cowboy Cowgirl Sportfishing Charters

Member since June 2014 Key West, United States
Background
Legendary Sportfishing in Key West – 60 Years Strong, Three Generations Deep! Step aboard one of our 6 premier fishing vessels, where 60 years of fishing excellence meets thrilling adventures in the world-renowned waters of Key West, FL. A family tradition spanning three generations, our fleet of six exceptional boats offers something for everyone – from seasoned anglers to families looking for an unforgettable day on the water. With a legacy of winning tournaments and creating lifelong memories, we specialize in offshore action for some of the most exciting species Key West has to offer. From bottom fishing to Offshore– our trips are all about chasing the big bites that make your heart race, whether it’s the dazzling Mahi Mahi, powerful Tuna, sleek Wahoo, or acrobatic Sailfish. A Fleet Built for Adventure Whether you’re looking for a luxurious offshore fishing experience or a shared group charter, our fleet is ready to deliver. Each boat is fully equipped with tournament-grade gear, spacious seating, and all the amenities you need for comfort and excitement on the water. From our iconic fleet, our vessels are helmed by captains with experience and unmatched knowledge of these legendary fishing grounds. Unmatched Expertise, Endless Thrills Fishing with our fleet isn’t just a trip – it’s a chance to learn from a team with generations of angling expertise. Our captains and crew know the waters of Key West like the back of their hand, and they’re here to ensure you have the trip of a lifetime. Whether it’s mastering trolling techniques, spotting fish, or simply enjoying the stunning views, we’ll make sure you leave with incredible memories. What’s Included: Top-tier equipment: Rods, reels, bait, tackle – we’ve got it covered. Family-friendly service: Trips suitable for anglers of all ages and experience levels. Catch care: Your captain will clean and fillet your catch for you. Comfort: Modern boats with shaded seating, clean restrooms, and plenty of space. Come fish with a team that’s been making dreams come true for six decades. Cowboy Cowgirl Sportfishing Charters is more than a fishing trip – it’s a slice of Key West history, filled with adventure, expertise, and passion. Book your trip today and discover why we’re one of the most celebrated names in Key West fishing!
Techniques
Our approach to fishing is versatile and adaptive, offering a range of techniques to suit the target species and conditions on any given day. From trolling and bottom fishing to reef and wreck fishing, we’re equipped to make every trip productive and enjoyable. The only type we don’t provide is flats fishing

Hey, we're Cowboy Cowgirl Sportfishing Charters

Key West, United States
Background
Legendary Sportfishing in Key West – 60 Years Strong, Three Generations Deep! Step aboard one of our 6 premier fishing vessels, where 60 years of fishing excellence meets thrilling adventures in the world-renowned waters of Key West, FL. A family tradition spanning three generations, our fleet of six exceptional boats offers something for everyone – from seasoned anglers to families looking for an unforgettable day on the water. With a legacy of winning tournaments and creating lifelong memories, we specialize in offshore action for some of the most exciting species Key West has to offer. From bottom fishing to Offshore– our trips are all about chasing the big bites that make your heart race, whether it’s the dazzling Mahi Mahi, powerful Tuna, sleek Wahoo, or acrobatic Sailfish. A Fleet Built for Adventure Whether you’re looking for a luxurious offshore fishing experience or a shared group charter, our fleet is ready to deliver. Each boat is fully equipped with tournament-grade gear, spacious seating, and all the amenities you need for comfort and excitement on the water. From our iconic fleet, our vessels are helmed by captains with experience and unmatched knowledge of these legendary fishing grounds. Unmatched Expertise, Endless Thrills Fishing with our fleet isn’t just a trip – it’s a chance to learn from a team with generations of angling expertise. Our captains and crew know the waters of Key West like the back of their hand, and they’re here to ensure you have the trip of a lifetime. Whether it’s mastering trolling techniques, spotting fish, or simply enjoying the stunning views, we’ll make sure you leave with incredible memories. What’s Included: Top-tier equipment: Rods, reels, bait, tackle – we’ve got it covered. Family-friendly service: Trips suitable for anglers of all ages and experience levels. Catch care: Your captain will clean and fillet your catch for you. Comfort: Modern boats with shaded seating, clean restrooms, and plenty of space. Come fish with a team that’s been making dreams come true for six decades. Cowboy Cowgirl Sportfishing Charters is more than a fishing trip – it’s a slice of Key West history, filled with adventure, expertise, and passion. Book your trip today and discover why we’re one of the most celebrated names in Key West fishing!
Techniques
Our approach to fishing is versatile and adaptive, offering a range of techniques to suit the target species and conditions on any given day. From trolling and bottom fishing to reef and wreck fishing, we’re equipped to make every trip productive and enjoyable. The only type we don’t provide is flats fishing
Our Team
Capt Woody (Sam) W.
Captain
Capt Cole B.
Captain
Sharky (Mark) B.
Business associate
Capt Cuzzy (Chris) B.
Captain

My Charter Listings

Excellent
4.7 / 5
(127 reviews)
Key West
 Instant Confirmation
Trips from US $850
Excellent
4.5 / 5
(369 reviews)
Key West
 5 bookings in the past week.
 Instant Confirmation
Trips from US $200
Excellent
4.6 / 5
(114 reviews)
Key West
 Instant Confirmation
Trips from US $950
Excellent
4.7 / 5
(8 reviews)
Stock Island
 Instant Confirmation
Trips from US $1,000
Excellent
4.1 / 5
(9 reviews)
Key West
 Instant Confirmation
Trips from US $1,100
Excellent
4.7 / 5
(25 reviews)
Stock Island
 Instant Confirmation
Trips from US $600

Fishing Reports

Customer reviews

Rating summary
Excellent
4.6 / 5
out of 5 stars from 652 reviews
Boat
Excellent
4.4 / 5
Crew
Excellent
4.7 / 5
Experience
Excellent
4.5 / 5
Photos & videos by reviewers (525)
Great Team
Irish Cowboy 3\/4 day trip
Irish Cowboy 3\/4 day trip
+522
Angler rating
469
117
30
15
11
Anglers claimed
Good experience
89%
Friendly captain
97%
Recommend this charter
90%
Appropriate for children
86%
Satisfied with the boat
93%
Caught fish
78%
Sort by:
Featured  
Showing:
5 of 652 reviews
Roberta T.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Irish Cowboy 3/4 day trip

VERIFIED   NEW  3/4 Day Trip โ€“ 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...
Roberta T. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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Roberta T. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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Robert B.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Awesome trip for a solo angler or a couple not looking to rent the whole boat

VERIFIED   NEW  3/4 Day Trip โ€“ Shared Charter (AM) on May 25, 2025
The captain and crew are awesome, the boat is clean and relatively comfortable. If you donโ€™t mind leaning on the rail a bit....
Robert B. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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Robert B. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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Agnes G.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Lived every min

VERIFIED   NEW  Full Day Trip โ€“ Shared Charter on May 30, 2025
I loved every minute of our trip with Paul and Chris. They were both amazing. They made it fun and my son just fell even more...
Agnes G. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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Agnes G. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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Daniel Y.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Father and son trip

VERIFIED   Half Day Trip (AM) Inshore on June 7, 2024
My son and I had a fantastic time on the Cowgirl II with Cowboy Cowgirl Sportfishing. The crewโ€™s expertise made our fishing...
Daniel Y. recommends Cowboy Cowgirl Sportfishing โ€“ Cowgirl II
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  Cowboy Cowgirl Sportfishing Charters Charter Operator replied

Oliver M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great Team

VERIFIED   NEW  Half Day Trip โ€“ Shared Charter (AM) on June 2, 2025
We had lots of fun on our first trip going fishing in the Ocean, I highly recommend this crew for your next Fishing trip.
Oliver M. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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Oliver M. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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