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    Key West Fishing Deals

    Key West Fishing Deals

    4.8 • 908 reviews
    Key West, FL

    Cowboy Cowgirl SportFishing Charters has been a trusted part of the Key West fishing scene since 1965, offering memorable days on the water for anglers of all experience levels. Known for experienced captains and a welcoming appro...

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    Book Key West Fishing Deals

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    Full-Day Key West Shared Deep Sea Fishing Charter

    Shared offshore fishing in Key West with a pro crew, max 6 passengers

    $411.66person
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    3-Hour Shark Fishing Charter in Key West

    Hands-on shark fishing in Key West for all ages

    $770.31
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    Private Deep Sea Fishing Charter in Key West

    Private offshore fishing for up to 6 on a fast, shaded 36-foot Hatteras

    From$1,175

    Review summary

    4.8
    Excellent
    908 reviews•Google Maps
    853
    17
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    Cowboy Charters consistently earns high praise from anglers of all skill levels, with families, first-timers, and seasoned fishers all walking away with great stories. The crew, particularly Captain Hans, Captain Sam, and Mate Larry, come up repeatedly in reviews for their knowledge of local waters, strong work ethic, and ability to put people on fish. Mahi-mahi, sailfish, grouper, mutton snapper, and tarpon are among the catches mentioned, and the crew cleans the fish for you before you head home. The atmosphere on board sounds genuinely fun and low-pressure. Beginners consistently mention feeling comfortable and well-coached, while experienced anglers appreciate the more technical challenge. Trips range from 4 to 8 hours, and the general consensus is that the crew stays focused and engaged throughout. One reviewer noted a skunked trip, a reminder that fishing is never guaranteed, but that experience stands out as the clear exception among an otherwise enthusiastic crowd. Most people leave already planning a return visit.

    What people are saying

    Review 1 of 5
    5/5

    We had the best day with Hans, Caleb and DJ! They worked hard to make sure we caught some Mahi and we caught 5!! It was a day we will remember and cherish as a family and when we visit KW again we will most def be looking them up for another trip!

    Photo of Rusty Ottaway

    Rusty Ottaway

    May 20, 2026

    Review 1 of 1
    5/5

    We had the best day with Hans, Caleb and DJ! They worked hard to make sure we caught some Mahi and we caught 5!! It was a day we will remember and cherish as a family and when we visit KW again we will most def be looking them up for another trip!

    Photo of Rusty Ottaway

    Rusty Ottaway

    May 20, 2026