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    1. Local experiences
    2. /Things to do in Key West…
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    4. /Sailing
    5. /3-Hour Private Sunset Sail In Key West
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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

    4.8 stars• 71 reviews

    Duration

    Three Hours

    Ideal For

    Up to 6 people

    Highlights

    Sail from Key West on a private sunset cruise for up to 6 guests. Choose your start time, play your music, and relax as you head to the crew’s favorite sunset spot.

    • Set your own departure time to fit your plans
    • Choose your music as you cruise toward sunset
    • Bring your own refreshments to enjoy onboard
    • Request custom meals based on a brief conversation
    • Return shortly after sunset or continue after dark

    Things to know

    Dress for the weather and expect to get wet on the sea. Follow the captain and crew’s safety instructions. If you plan to scuba dive or snorkel, bring your certification card.

    Cancellation Policy

    Fully paid reservations are refundable, less 30%, when you cancel at least 6 months prior to your scheduled trip. All other refund requests are subject to management approval. When approved, refunds are issued usually within 4 business days.

    Product ID: TGWNWM

    FAQs

    Bring up to 6 guests.

    Dress for the weather and wear clothes you do not mind getting wet. Bring sunscreen, a floppy hat, boat shoes, and a swimsuit if you want. Bring any refreshments you’d like to enjoy onboard.

    Yes. Follow the captain and crew’s instructions for everyone’s safety.

    Meeting details

    Pier C-18, 120 Margaret St., Key West, FL 33040

    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

    Private Charter - ARIA

    $1,634.40

    42 ft Catamaran

    0

    Private Charter - ZODIAC

    $2,996.40

    60ft Fountaine Pajot Catamaran

    0

    Why book through Greetwell?

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      No booking or service fees, ever

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

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      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.8
    Excellent
    71 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 4
    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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