Cowboy Cowgirl Sportfishing Charters

Rating

Anglers' gallery (638)

What anglers say

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  Georgina Simonson

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  Florida, US

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  Member since 2026

  5.0

  Verified

  10/10 recommend!

  3/4 Day Trip – Shared on August 22, 2026 • 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.

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  Loretta Daniel

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  Kentucky, US

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  Member since 2025

  5.0

  Verified

  Difficult week but Cowboy Cowgirl came through

  Full Day Trip – Shared Charter on December 15, 2025 • 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

  January 18, 2026

  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.

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  Dave Foley

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  Washington State, US

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  Member since 2026

  5.0

  Verified

  Had the best time!!!

  Full Day Trip on September 4, 2026 • 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.

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  Thomas Wondrock

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  Oklahoma, US

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  Member since 2026

  5.0

  Verified

  Amazing time

  Full Day Trip – Shared Charter on June 6, 2026 • 2 adults

  The 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.

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  Response from Charter operator

  June 17, 2026

  Thank you, Thomas, for the outstanding review and for spending the day with us aboard the Cowboy Cowgirl 36’ Hatteras! We’re thrilled to hear you had such a successful trip and that DJ made such a lasting impression. Our mates work incredibly hard behind the scenes, and DJ’s nonstop effort, attention to detail, and dedication to keeping guests on fish are exactly what we strive for every day. We’ll be sure to pass along your kind words to him. It’s great to hear the group caught plenty of fish and even got to enjoy feeding the giant tarpon at the dock afterward. Those extra moments often become some of the most memorable parts of a Key West fishing adventure. We truly appreciate your recommendation and hope you’ll join us again for another Shared Fishing Charter, a Private Offshore Fishing Charter, or even one of our exciting Shark Fishing Adventures. And don’t forget—go to BiteBackBrand and under Local Legends, go to Cowboy to get your t-shirts and other gear. Thanks again for fishing with Cowboy Cowgirl Sportfishing. We look forward to seeing you back in Key West soon!

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  Curt Weldon

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  Kansas, US

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  Member since 2025

  5.0

  Verified

  Great Experience

  Half Day Trip – Shared Charter on December 23, 2025 • 1 adult

  Want to thank the crew of the Sanctuary for providing me with a great experience. My first fishing trip was rescheduled due to rough waters and I went out the very next day. Took us into the Atlantic Ocean, just past the reefs. The crew showed their prowess by getting us on fish right away. Caught many yellow tails, macerals and even a barracuda. We also saw several sharks. This was a once in a lifetime experience for me and it was fantastic. Thank you so much.

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  Response from Charter operator

  January 18, 2026

  Curt, thank you for the stellar review and for rolling with the weather call. Safety comes first, and we’re glad we were able to get you back out the very next morning. Hearing that the Sanctuary crew put you right on the bite beyond the reef—yellowtail, mackerel, a toothy barracuda, plus multiple shark sightings—makes our day. That’s a great mixed-bag half-day on a shared charter in Key West, and we’re honored it felt “once in a lifetime.” We’d love to have you back anytime. If you want to focus on big toothy critters next visit, we run dedicated Key West shark fishing adventures (inshore, reef, and deepwater). Or, choose a private charter for a fully customized plan with your own crew and pace. Also, for a keepsake from the day, 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 the forecast looks rough on my day? A: We monitor marine conditions closely. If it’s unsafe or not enjoyable, we’ll reschedule you to the next safe window at no extra charge. Q: What’s the difference between a shared and a private charter? A: Shared trips let solo anglers or small parties split the boat and cost with others—great value and steady action. Private trips reserve the whole boat for your group, with a custom plan (targets, style, pace) and flexibility to change tactics on the fly.