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    Restless Native Charters

    Restless Native Charters

    4.9 • 69 reviews
    Key West, FL

    Restless Native Charters offers private luxury sailing adventures designed to help guests experience the Florida Keys at their own pace. From relaxed sunset sails and snorkeling excursions to overnight expeditions and custom speci...

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    Book Restless Native Charters

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    Sail the Florida Keys on a 12-Hour Charter

    Spend a full day sailing from Key West with up to 6 guests

    From$3,677
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    Sail & Snorkel on a 4-Hour Key West Charter

    Sail Key West waters on a private 4-hour charter for up to six guests

    From$1,906
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    3-Hour Private Sunset Sail In Key West

    Private Key West sunset sail with your music and a flexible start time

    From$1,634

    What people are saying

    Review 1 of 5
    5/5

    We had a phenomenal time! Captain Brad and Maddie were absolutely incredible. Brad is such a great captain—so fun, funny, and incredibly knowledgeable about Key West. He took us to a fantastic sandbar area where we did a lazy river and just hung out; we had an absolute blast. Maddie was fabulous and so pleasant, constantly serving us delicious drinks and lunch throughout the day. The boat itself is gorgeous. It’s brand new, beautiful, and had absolutely everything we needed. We honestly felt like celebrities on a private excursion! My friends and I have been talking about it ever since, and it was easily the highlight of our trip. Thank you for a 10/10 experience! 🛥️🌴🍹

    Photo of Mark Rukavina

    Mark Rukavina

    May 17, 2026

    Review 1 of 1
    5/5

    We had a phenomenal time! Captain Brad and Maddie were absolutely incredible. Brad is such a great captain—so fun, funny, and incredibly knowledgeable about Key West. He took us to a fantastic sandbar area where we did a lazy river and just hung out; we had an absolute blast. Maddie was fabulous and so pleasant, constantly serving us delicious drinks and lunch throughout the day. The boat itself is gorgeous. It’s brand new, beautiful, and had absolutely everything we needed. We honestly felt like celebrities on a private excursion! My friends and I have been talking about it ever since, and it was easily the highlight of our trip. Thank you for a 10/10 experience! 🛥️🌴🍹

    Photo of Mark Rukavina

    Mark Rukavina

    May 17, 2026