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
(129 reviews)
Key West
 Last booking: 2 days ago
 Instant Confirmation
Trips from US $850
Excellent
4.5 / 5
(387 reviews)
Key West
 Last booking: 9 hours ago
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
 Last booking: 6 days ago
 Instant Confirmation
Trips from US $600

Fishing Reports

Customer reviews

Rating summary
Excellent
4.6 / 5
out of 5 stars from 672 reviews
Boat
Excellent
4.4 / 5
Crew
Excellent
4.7 / 5
Experience
Excellent
4.5 / 5
Photos & videos by reviewers (541)
Great trip!
Great trip!
Great trip!
+538
Angler rating
484
117
33
16
11
Anglers claimed
Good experience
89%
Friendly captain
97%
Recommend this charter
89%
Appropriate for children
86%
Satisfied with the boat
92%
Caught fish
78%
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Showing:
5 of 672 reviews
Jack M.

The captain canceled

VERIFIED   January 3, 2021
The charter operator canceled on trip date. This is an automated posting.
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4 persons find this review helpful
You and 4 people found this review helpful
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You and 4 people found this review helpful

Christopher V. B.
Independence Charter Town, MI
Good
2.3 / 5
Experience:
Bad
2.0 / 5
Boat
Good
3.0 / 5
Crew
Bad
2.0 / 5
Overall

July

VERIFIED   3/4 Day Trip โ€“ Shared Charter (AM) on July 7, 2020
No captain Mark, no air conditioning, not many fish!ย  The crew did work at it, it was extremely hot day!ย  Sure wouldโ€™ve...
Christopher V. B. does not recommend Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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Christopher V. B. does not recommend Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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Leon J. M.
United States
Very good
3.7 / 5
Experience:
Good
3.0 / 5
Boat
Excellent
5.0 / 5
Crew
Good
3.0 / 5
Overall

Key West Adventure

VERIFIED   3/4 Day Trip โ€“ Shared Charter (AM) on October 18, 2016
Didnโ€™t catch anything worth keeping. Tried but not hard enough. Not all crews fault.
Leon J. M. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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Leon J. M. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
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JOHN R.
Rockledge, FL
Bad
2.0 / 5
Experience:
Poor
1.0 / 5
Boat
Good
3.0 / 5
Crew
Bad
2.0 / 5
Overall

3/4 day trip on Irish cowboy

VERIFIED   3/4 Day Trip (AM) on April 13, 2021
it was a good thing we did not have any women in our group. There was no working toilet.
JOHN R. does not recommend Cowboy Cowgirl Charters โ€“ Irish Cowboy
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JOHN R. does not recommend Cowboy Cowgirl Charters โ€“ Irish Cowboy
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Krzysztof Z.
Good
2.3 / 5
Experience:
Poor
1.0 / 5
Boat
Very good
4.0 / 5
Crew
Bad
2.0 / 5
Overall

Fishing with Michelle

VERIFIED   3/4 Day Trip โ€“ Shared Charter (AM) on January 29, 2021
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1 person finds this review helpful
You and 1 other person found this review helpful
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1 person finds this review helpful
You and 1 other person found this review helpful