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    Island to Island Charters

    Island to Island Charters

    5.0 • 190 reviews
    Key West, FL

    Island to Island Charters offers a refreshing way to experience Key West, with personalized eco-adventures designed to showcase the natural beauty of the Florida Keys. From dolphin watching and snorkeling to secluded sandbars, she...

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    Book Island to Island Charters

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    3-Hour Private Charter in Key West

    Customize a private boat outing with snorkeling, fishing, island stops, and sunset cruising

    $624.25
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    4-Hour Private Charter in Key West

    Customize your time on the water with snorkeling, fishing, island stops, or a sunset cruise

    $737.75
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    6-Hour Private Charter in Key West

    Customize your day on Key West’s waters with snorkeling, fishing, or island exploring

    $964.75
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    Cruise Key West at Sunset on a Private Charter

    Private Key West sunset cruise for up to 6 on the Miss Marie

    $482.38

    Review summary

    5.0
    Excellent
    190 reviews•Google Maps
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    Captain Ally has built a serious reputation in the Keys for knowing exactly where to take people and what to look for once you're out there. Reviewers consistently rave about her wildlife spotting skills, with sightings ranging from dolphins, manatees, and sea turtles to multiple shark species, eagle rays, and even the occasional manatee. She also knows her shelling spots, and guests regularly come back with more than they expected. What stands out across the reviews is how personal the experience feels. Ally keeps things relaxed and unhurried, and her genuine passion for the local ecosystem comes through in how she guides the trip. She's also great with kids, and families mention how engaged everyone stayed throughout. Options include shelling trips, eco tours, snorkeling, sandbars, sunset cruises, and fishing, so there's flexibility depending on what you're after. The reviews here are overwhelmingly positive with zero notable complaints, which is rare. Repeat customers show up frequently in the comments, which says a lot. If you're trying to get off the beaten path and see the Keys from the water with someone who actually knows it well, Ally is a strong choice.

    What people are saying

    Review 1 of 5
    5/5

    Captain Ally was honestly the best captain we’ve ever had! It felt like we were going out with a family member on the boat! She took us to the sandbar and then snorkeling! Seen a lot of wildlife!

    Photo of Kaitlin Oxendine

    Kaitlin Oxendine

    July 6, 2026

    Review 1 of 1
    5/5

    Captain Ally was honestly the best captain we’ve ever had! It felt like we were going out with a family member on the boat! She took us to the sandbar and then snorkeling! Seen a lot of wildlife!

    Photo of Kaitlin Oxendine

    Kaitlin Oxendine

    July 6, 2026