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    1. Local experiences/
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    5. Sail & Snorkel on a 4-Hour Key West Charter
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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

    4.9 stars• 69 reviews
    From$1,906incl. taxes and fees

    Duration

    Four Hours

    Ideal For

    Up to 6 people

    Highlights

    Spend four hours sailing out of Key West with your group. Swim, snorkel, free dive, or relax on floaties as you cruise to favorite spots.

    • Charter a private sail for up to six people
    • Swim, snorkel, or free dive during your time on the water
    • Relax on floaties and enjoy time at sea
    • Bring your own food and beverages for the trip
    • Return to the dock after four hours for your next plans

    Things to know

    Be on time since you sail only for the time you booked. Follow the captain and crew’s instructions for safety. If you plan to scuba, bring your certification and gear.

    Cancellation Policy

    Fully paid reservations are refundable, less 30% with cancellation notice at least 6 months prior to your scheduled trip. All other refund requests are subject to management approval.

    FAQs

    Book for a maximum of six people.

    Bring your own food and beverages. Additional food is available upon request.

    Dress for the weather and plan to get wet. Bring sunscreen, a hat, a camera, and boat shoes. Bring a swimsuit if you want to swim.

    Experience provided by Restless Native Charters
    Experience provided by Restless Native Charters

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #QUDE7N

    Private Charter - ARIA

    $1,906.80

    42 ft Catamaran

    0

    Private Charter - ZODIAC

    $3,268.80

    60ft Fountaine Pajot Catamaran

    0

    Why book through Greetwell?

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      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.9
    Excellent
    69 reviews•Google Maps
    66
    0
    1
    1
    1

    Captain Brad and Maddie are the real draw here, and it shows in nearly every review. Guests consistently rave about their warmth, humor, and genuine expertise on the water. Brad handles navigation and local knowledge while Maddie keeps guests comfortable with food, drinks, and dolphin spotting tips. The boat itself, a 60-foot catamaran called Zodiac, is described as spotless and well-appointed with thoughtful touches like beanbag loungers and Bluetooth speakers. What stands out most is how personalized each trip feels. Reviewers mention proposals, birthday celebrations, holiday fireworks, and even a Bahamas sailing week, suggesting Brad and Maddie are equally comfortable with quick day sails and longer adventures. The food and drinks receive consistent praise, and the crew's attention to safety comes up often without ever feeling rigid or overly formal. With a near-perfect rating across a strong volume of reviews, this is clearly a team that takes pride in the experience they deliver.

    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

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