Cowboy Cowgirl SportFishing Charters
    Est. 1965 · Key West, Florida

    In the Bite

    Fishing Reports, Field Guides & Stories from Key West's Most Experienced Captains

    Latest Reports & Field Notes

    Fishing TipsAug 25, 2026

    Dog-Friendly Fishing Charter Tips for Key West

    Bringing your dog on a Key West fishing charter is easier than most people think. Here is what to pack, how to tell if your dog is a good fit, and what the day looks like.

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    Fishing TipsAug 25, 2026

    Is Key West Dog-Friendly? A Visitor's Guide

    Key West is one of the more dog-friendly destinations in Florida, from beach access to outdoor dining. Here is what to know before you travel with your dog.

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    Charter GuideJul 1, 2026

    Key West Party Boat vs. Private Fishing Charter: Which is Better?

    Party boats are cheap but crowded. Private charters give you the whole boat but cost more. Here's an honest side-by-side — and why a shared sportfishing charter is often the sweet spot for solo travelers and couples.

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    Charter GuideMay 3, 2026

    Wreck Fishing Key West: Target Big Fish Around Structure

    Wreck fishing in Key West is one of the most productive and exciting ways to fish — structure-rich water that holds grouper, snapper, amberjack, and more, year-round.

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    Shark FishingFeb 28, 2026

    Shark Fyve™ — The Ultimate Challenge

    This is not hype. This is real water, real predators, and real strategy. Shark Fyve™ in Key West represents the highest level of respect for the ocean's apex predators — and for those willing to put in the time, the pursuit has just begun.

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    Fishing TipsFeb 2, 2026

    Shared vs Private Fishing Charters in Key West

    Deciding between a shared or private fishing charter in Key West? This guide breaks down the key differences in cost, flexibility, and experience so you can choose the right option for your trip.

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    Fishing RegulationsFeb 2, 2026

    Key West Shark Fishing Regulations (2026): What's Legal

    Key West shark fishing rules explained: licenses, legal gear, closed species, shore vs boat rules, and best practices for safe catch-and-release in the Florida Keys.

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    Travel GuideJan 19, 2026

    Is Key West Worth It? An Honest Look at What to Expect

    Key West is worth it if you know what you're coming for. It's not a traditional beach vacation, not a mega-resort destination, and not just a party island. Key West is about being on the water, slowing down, and experiencing the Florida Keys lifestyle.

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    Fishing TipsNov 28, 2025

    Affordable Fishing Charter Key West

    Book affordable Key West fishing charters with private and shared trips. Offshore, inshore, reef, and shark fishing. Family-owned since 1965.

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    Fun & CultureOct 1, 2025

    Bananas: Fishing Superstitions from the Key West Docks

    You ever hear someone say 'good luck' before a fishing trip… and then not catch a single thing all day? Here in Key West, we fish by feel, by tide… and by a few weird rules passed down from old salty legends.

    Read: Bananas: Fishing Superstitions from the Key West Docks