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    Island to Island Charters

    Island to Island Charters

    5.0 • 199 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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    Private Key West Island Hopping & Snorkel Boat Charter

    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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    Private Sunset Cruise on a 23' Deck Boat in Key West

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

    $482.38

    Review summary

    5.0
    Excellent
    199 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

    I have spent time with Captain Ally throughout my trips to Key West and she does not disappoint! This trip I took my 6-year old granddaughter on her first snorkeling adventure. Captain Ally took the time to work with her getting her accustomed to the snorkeling experience on a shallow sandbar first before heading to the reef. At the reef she had the experience of a lifetime — swimming near an extremely large sea turtle! I would recommend Island to Island Charters for people of all experiences! Your day will the most memorable one of your trip!

    Photo of Gretchen Sparks

    Gretchen Sparks

    August 20, 2026

    Review 1 of 1
    5/5

    I have spent time with Captain Ally throughout my trips to Key West and she does not disappoint! This trip I took my 6-year old granddaughter on her first snorkeling adventure. Captain Ally took the time to work with her getting her accustomed to the snorkeling experience on a shallow sandbar first before heading to the reef. At the reef she had the experience of a lifetime — swimming near an extremely large sea turtle! I would recommend Island to Island Charters for people of all experiences! Your day will the most memorable one of your trip!

    Photo of Gretchen Sparks

    Gretchen Sparks

    August 20, 2026