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Cowboy Cowgirl Sportfishing Charters
Charter operator

Cowboy Cowgirl Sportfishing Charters

Key West, United States
Federal waters
500+ reviews
Legendary Sportfishing in Key West: 60 Years Strong, Three Generations Deep! Step aboard one of our six 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 fishing, 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. Our vessels are helmed by experienced captains with 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 backs of their hands, 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, and tackle are provided. Family-friendly service: Trips are 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.
Capt Woody (Sam) W.
Captain
Capt Cole B.
Capt Cole B.
Captain
Sharky (Mark) B.
Sharky (Mark) B.
Business partner
Capt Cuzzy (Chris) B.
Capt Cuzzy (Chris) B.
Captain

Charters

Rating

4.6
737 reviews
4.4
Boat & Equipment
4.7
Captain & Crew
4.5
Fishing Experience

What anglers say

88%
Good experience
97%
Friendly captain
91%
Recommend this charter
86%
Appropriate for children
92%
Satisfied with the boat
78%
Caught fish

All reviews (737)

Showing 1 – 5 of 737 reviews
  • Daniel Else
    Daniel Else
    Repeat angler
    gb
    United Kingdom
    Member since 2025
    2 trips
    5.0
    Verified
    NEW

    one of my target species achieved!

    3/4 Day Trip – Shared • 1 adult

    there 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 Simonson
    Georgina Simonson
    us
    Florida, US
    Member since 2026
    5.0
    Verified

    10/10 recommend!

    3/4 Day Trip – Shared • 2 adults

    I 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:
    Dolphin (Mahi Mahi)
    Great Barracuda
  • Loretta Daniel
    Loretta Daniel
    us
    Kentucky, US
    Member since 2025
    5.0
    Verified

    Difficult week but Cowboy Cowgirl came through

    Full Day Trip – Shared Charter • 2 adults

    We 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 operator

    Loretta, 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.

  • Anthony Chapman
    Anthony Chapman
    us
    Indiana, US
    Member since 2025
    5.0
    Verified
    NEW

    Great Crew And Day On The Water

    3/4 Day Trip (PM) • 2 adults

    The bite was slow on the big fish, but caught some great eaters. The crew was very professional and did their best to get us bites. I would recommend them to anyone looking to get out for a day on the water.

    Response from Charter operator

    Thank you, Tony, for the fantastic 5-star review and for sharing your photos! We’re so glad you enjoyed your 6-hour fishing charter aboard the Irish Cowboy! Some days the big fish are hungry, and other days they make us work a little harder! That’s part of the adventure of deep sea fishing in Key West. We’re happy our crew’s professionalism and determination made your day enjoyable, even with a slower bite on the bigger fish. And bringing home some great eating fish is always a nice bonus! Our captains and mates work hard to give every guest the best fishing experience possible, regardless of what the ocean has planned for the day. Thank you for recommending Cowboy Cowgirl Sportfishing Charters, proudly family-owned and operated in Key West since 1965. We appreciate you fishing with us and look forward to welcoming you back aboard the Irish Cowboy for another offshore fishing adventure in the Florida Keys!

  • Dave Foley
    Dave Foley
    us
    Washington State, US
    Member since 2026
    5.0
    Verified

    Had the best time!!!

    Full Day Trip • 4 adults

    The 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:
    Dolphin (Mahi Mahi)
    Wahoo

Real catches shared by our community

  • Cowboy Cowgirl 36 Ft Hatteras--Since 1965
    Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
    Large billfish, likely a sailfish, swimming alongside a charter boat in open blue water during an active fight.
    Fish 1
    Fish 2
    +2
    Sailfish
    Daniel E.
    Daniel E.
    there 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!
  • Cowboy Cowgirl Charters – Irish Cowboy
    Cowboy Cowgirl Charters – Irish CowboyKey West, FL
    Multiple fish hung on a display rail aboard a charter boat at a nighttime marina, with an adult crew member visible in the background.
    Fish 1
    Fish 2
    +1
    Jack Crevalle
    Anthony C.
    Anthony C.
    The bite was slow on the big fish, but caught some great eaters. The crew was very professional and did their best to get us bites. I would recommend them to anyone looking to get out for a day on the water.
  • Cowboy Cowgirl 36 Ft Hatteras--Since 1965
    Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
    Anglers bring a colorful mahi-mahi aboard a fishing boat in open ocean waters, with rods and tackle visible on deck.
    Fish 1
    Fish 2
    Dolphin (Mahi Mahi)
    Salvatore M.
    Salvatore M.
    3 mahi mahi, 1 skipjack, 1 barracuda
  • Cowboy Cowgirl 36 Ft Hatteras--Since 1965
    Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
    Angler proudly displaying two large Wahoo fish at the dock after a successful fishing trip.
    Jason W.
    Jason W.
    Great time...but time was short. Paid for 6hrs got a little under 3hrs. Lightning 🌩 it happens was truly saddened the weather ended our trip. First mate Tyson was great worked hard while we fished.
  • Cowboy Cowgirl 36 Ft Hatteras--Since 1965
    Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
    A young angler proudly displaying a large Mahi Mahi while fishing offshore, showcasing the excitement of a successful catch.
    Fish 1
    Fish 2
    Dolphin (Mahi Mahi)
    Merijn L.
    Merijn L.
    We 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
  • Cowboy Cowgirl 36 Ft Hatteras--Since 1965
    Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
    Angler joyfully displaying a vibrant Mahi Mahi on a fishing boat, showcasing a successful day on the water.
    Fish 1
    Fish 2
    Dolphin (Mahi Mahi)
    Brad C.
    Brad C.
  • Cowboy Cowgirl Charters – Irish Cowboy
    Cowboy Cowgirl Charters – Irish CowboyKey West, FL
    Angler poses beside a large barracuda hanging from a dockside fish display board, with charter boats visible in the marina.
    Dave F.
    Dave F.
    The 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.
  • Cowboy Cowgirl 36 Ft Hatteras--Since 1965
    Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
    Multiple mahi-mahi displayed on a boat fillet table, with bright yellow-green coloring and blue spots visible.
    Fish 1
    Dolphin (Mahi Mahi)
    Georgina S.
    Georgina S.
    I 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.
  • Cowboy Cowgirl 36 Ft Hatteras--Since 1965
    Cowboy Cowgirl 36 Ft Hatteras--Since 1965Key West, FL
    A couple proudly displaying their catch of Mahi Mahi at the dock, enjoying a sunny day on the water.
    Fish 1
    Dolphin (Mahi Mahi)
    Haley R.
    Haley R.
    Loved them! Most relaxing day in the sun and caught some Maui Maui which is what I was hoping for
  • Cowboy Cowgirl-Cold AC 45 Ft Hatteras
    Cowboy Cowgirl-Cold AC 45 Ft HatterasKey West, FL
    Group posing beneath a row of freshly caught fish on a display rack at a Key West marina.
    Fish 1
    Dolphin (Mahi Mahi)
    Jared D.
    Jared D.
    Calab, the mate, necer stopped workimg. we chartered for 12 hours ahd he never stopped. if yuu want a great experince with a crew that goes over top make sure to DEMAND Captain Hans and mate Calab for your fishing trip.

Our Fishing Locations

What's biting with Cowboy Cowgirl-Cold AC 45 Ft Hatteras in Key West

Reef fishing is still good but can be windy. Bonefish thins out on the flats but Permit is as good as ever. Sailfish and Tuna are caught over the reefs and backcountry fishing is excellent.

Top catches for November

Fishing reports

An angler proudly displaying a large Amberjack while fishing on a boat in clear blue waters.

Legendary Catch in Key West – Trophy Afr

Feb 25, 2025 • Key West
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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A young angler proudly displaying a large Wahoo while fishing offshore, showcasing a beautiful day on the water.

Mixed Bag & a Trophy Wahoo – Key West Fi

Feb 19, 2025 • Key West
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 • Key West
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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Angler reeling in a large fish while fishing from a boat in clear blue waters, showcasing an exciting moment on the water.

Bucket List Trophy – Sailfish Caught Cow

Feb 14, 2025 • Key West
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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An angler proudly displaying a large shark caught during a fishing trip, with a scenic marina backdrop.

Cobia Action Heats Up – Key West Fishing

Feb 11, 2025 • Key West
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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Two anglers proudly displaying a large Giant Trevally on a fishing charter in open waters.

Unforgettable Catch – African Pompano on

Feb 11, 2025 • Key West
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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