Key West
Instant Confirmation
Trips from
US $1,200
Charter operator
Cowboy Cowgirl Sportfishing Charters
Ki Vest, Sjedinjene Države
Federal waters
500+ reviews
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!
Capt Woody (Sam) W.
kapetan
Capt Cole B.
kapetan
Sharky (Mark) B.
Poslovni saradnik
Capt Cuzzy (Chris) B.
kapetan
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Rating
4.6
730 reviews
4.4
Boat & Equipment
4.7
Captain & Crew
4.5
Fishing Experience
Anglers' gallery (631)
What anglers say
88%
Dobro iskustvo
97%
Prijatan kapetan
91%
Preporučite ovaj čarter
86%
Prikladno za decu
92%
Zadovoljni brodom
78%
Uhvate ribe
All reviews (730)
Showing 1 – 5 of 730 reviews
Caleb Woods
Gruzija, Сједињене Државе•Član od 2026The captain canceled
Trip was supposed to happen on avgust 20, 2026The charter operator canceled on trip date. This is an automated posting.
Georgina SimonsonFlorida, Сједињене Државе•Član od 20265.0VerifiedNEW10/10 recommend!
3/4 Day Trip – Shared • 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.
Reported catch:
Dave FoleyWashington State, Сједињене Државе•Član od 20265.0VerifiedNEWHad the best time!!!
Full Day Trip • 4 adultsThe crew was the best. The Captain did a fantastic job reading the Gulf Stream and knowing where tge fish were. Tge deck hand (Caleb) worked his butt off for my family and I. he kept us entertained and was patient with some of the members who had never fished before. My son caught a betiful Wahoo, which is being mounted. we are definitely coming back.
Reported catch:
Loretta DanielKentaki, Сједињене Државе•Član od 20255.0VerifiedDifficult week but Cowboy Cowgirl came through
Full Day Trip – Shared Charter • 2 adultsWe went to Key West just for the fishing trip then wind came up and nothing could go out. They worked with us and took us out our last day. We had hoped for some big boys, sailfish, etc but at this point we just wanted to have fun. The captain Hans managed some rough water and our first mate worked hard to help us all catch fish and that we did. Lots of maceral, snapper and yellow tail and even the odd mutton and blue wrasse. When we got back they were waiting to drive us to the airport to catch our flight. I can't recommend enough how hard they worked to make our trip good and get fish.
Response from Charter operatorLoretta, thank you for the kind words—and for rolling with a windy week. We’re glad we could shift your date and still get you out on your last day. Captain Hans and our first mate work hard to keep things safe, steady, and fun when the weather kicks up, and it’s great to hear everyone hooked fish—mackerel, snapper, yellowtail, even a mutton and blue wrasse. Getting you to the airport on time was the easy part. We appreciate you choosing our Key West fishing charter and hope to chase those “big boys” (including sailfish) with you next time. If you’re planning a return, we run both shared and private charters—pick what fits your group—and we also offer Marquesas Key historical fishing tours for a special day off the beaten path. Also, if you want a keepsake from the trip, go to BiteBackBrand and under Local Legends, go to Cowboy to get your t-shirts and other gear. —Michelle & the Cowboy Cowgirl Sportfishing team Helpful Q&A Q: What happens if wind or weather cancels my trip? A: Safety comes first. We monitor forecasts and, if conditions aren’t safe or enjoyable, we’ll reschedule you to the next safe window or help you choose an alternate trip style that fits the seas. Q: When’s the best time to target sailfish in Key West? A: Late fall through early spring is prime, especially around cold fronts. Tell us your dates and we’ll recommend the best charter (and tactics) to maximize your shot.
Darin AlanKentaki, Сједињене Државе•Član od 20265.0Verified5 Star Experience
12 Hrs SwordFishing-Serious Anglers • 4 adultsCapt Nels and mates Daniel & Caleb were awesome! Winds were crazy, seas were rowdy and they still put us on the fish. I think we used every reel on the boat, trying many techniques, and put us on 2 massive sailfish off the kites. Very knowledgeable and willing to teach along the way which I really appreciate as an amateur angler myself. We will be back this summer to get out to the wall and get that next bucket list fish!
Reported catch:
Real catches shared by our community
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- Cowboy Cowgirl-Cold AC 45 Ft HatterasKey West, FL
- Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
- Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
- Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
- Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
- Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
Our Fishing Locations
What's biting with Cowboy Cowgirl-Cold AC 45 Ft Hatteras in Key West
Vreme se hladi i gužve se proređuju. Ovo je najbolje doba godine za Slam na plićacima. Vreme može biti nepredvidivo sa uraganima, ali pecanje čini sve vrednim truda.
Top catches for septembar
Fishing reports
Legendary Catch in Key West – Trophy Afr
feb 25, 2025 • Ki Vest
Some catches are just legendary—and this African Pompano is one of them! The bite is on, and there’s no better time to get out on the water. Who’s ready to make their own legend? Let’s go fishing!
#LegendaryCatch #AfricanPompano #KeyWestFishing #CowgirlCharters #FishingAdventures #OffshoreFishing #DeepSeaFishing #SportFishing #TrophyFish #FishingSeason #ReelLegends”
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Mixed Bag & a Trophy Wahoo – Key West Fi
feb 19, 2025 • Ki Vest
Another fantastic day of Key West sportfishing, with a great variety of fish hitting the deck! The highlight of the trip was a beautiful Wahoo, always an exciting catch. Along with that, our anglers landed a solid mix of species, making for an action-packed day on the water.
The bite is hot, and now’s the time to get in on the action! Whether you’re looking for a shared or private charter, there’s no better way to experience the thrill of fishing in Key West. Book your trip online and let’s get after it!
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Key West Fishing Report – Action-Packed
feb 14, 2025 • Ki Vest
The bite has been ? offshore, and we’ve been landing some beautiful fish! ? Our latest trip brought in an impressive mahi that put on quite the show. The waters around Key West are teeming with life, making this the perfect time to get out on the water.
Whether you’re looking to chase sailfish, wahoo, mahi-mahi, tuna, or snapper, we’ve got the trip for you! We also offer shark adventures (inshore, reef, and deepwater), fishing and sandbar combo trips, and even historical Marquesas Key fishing tours for those looking to explore beyond the usual spots.
Book your adventure today and experience the best of Key West fishing! ??
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Bucket List Trophy – Sailfish Caught Cow
feb 14, 2025 • Ki Vest
February fishing in Key West keeps delivering incredible moments! On a recent shared charter, one lucky angler checked a bucket-list fish off with a beautiful Sailfish. The fight was unforgettable, and seeing this trophy fish up close as it came over the side was the highlight of the trip. Nothing beats the thrill of catching one of the ocean’s most iconic game fish!
Whether you’re looking for a shared or private charter, there’s no better time to get out on the water and experience Key West sportfishing at its best.
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Cobia Action Heats Up – Key West Fishing
feb 11, 2025 • Ki Vest
It was a Cobia kind of day on the water! These powerful fish kept us busy, giving our anglers an exciting fight and some great table fare. The bite was steady, and the conditions were perfect for another successful Key West fishing trip.
Whether you're looking for a shared or private charter, a trip to the Marquesas Keys, a shark adventure, or a fishing and sandbar combo, now’s the time to get out and enjoy the action!
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Unforgettable Catch – African Pompano on
feb 11, 2025 • Ki Vest
Fishing is for everyone, and today was proof of that! We had the absolute pleasure of taking out a determined angler in a wheelchair, and he made the most of it—landing an amazing African Pompano, a true trophy catch. Watching him reel in his prize fish was an incredible moment, and our experienced Master Captains were there every step of the way to ensure he had a smooth and enjoyable trip.
We’re always happy to accommodate anglers of all abilities and make sure everyone gets a shot at the thrill of Key West sportfishing. Whether you're looking for a shared or private charter, we’re here to make it happen!
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