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    1. Local experiences
    2. /Things to do in Key West…
    3. /Water Activities
    4. /Sailing
    5. /Key West Full-Day Sailing Charter
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    Key West Full-Day Sailing Charter

    Spend eight hours sailing, snorkeling, and diving from a private Key West catamaran

    4.8 stars• 71 reviews
    From$2,451incl. taxes and fees

    Duration

    8 hrs

    Ideal For

    Up to 6 people

    Includes

    Snorkeling gear, towels, guides

    Highlights

    Spend eight hours at sea on a private sailing catamaran in Key West. Plan a day of sailing, snorkeling, scuba diving, and other on-water adventures.

    • Sail for eight hours aboard a private catamaran
    • Snorkel during your day on the water
    • Dive with scuba equipment if you bring your certification and gear
    • Enjoy guided tours in and out of the water

    What's Included

    • Snorkeling gear
    • Towels
    • Guided tours in and out of the water

    Know before you go

    • Arrive on time; the charter sails only for the time booked
    • Follow the captain and crew's safety directions
    • Bring scuba certification and gear if you plan to scuba dive
    • A fuel, dockage, and insurance surcharge applies; gratuity is not included. Clarify the surcharge amount with Greetwell before booking

    Cancellation Policy

    Cancel at least 6 months before your trip for a refund minus 30%. Other refund requests require management approval.

    FAQs

    No. A 15% gratuity is customary. If you do not provide gratuity in cash or by Venmo, a 15% gratuity will be assessed at the completion of your charter using the card on file.

    Bring weather-appropriate clothes that can get wet, sunscreen, a floppy hat, boat shoes, and an optional swimsuit. Bring your scuba certification and gear if you plan to scuba dive.

    Yes. You must select the number of children under 13 in your party when booking the sailing charter.

    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 #3F9ZT7

    Private Charter - ARIA

    $2,451.60

    42 ft Catamaran

    0

    Private Charter - ZODIAC

    $3,813.60

    60ft Fountaine Pajot Catamaran

    0

    Why book through Greetwell?

    • No Added Fees

      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

    4.8
    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 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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