Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Key West…
    3. /Water Activities
    4. /Yacht Charters
    5. /Custom Sailing Charter in Key West
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 1
    Product image 2
    Gallery image 1
    Gallery image 2

    Custom Sailing Charter in Key West

    Tailor a private Caribbean sailing charter for your celebration or getaway

    4.8 stars• 71 reviews
    From$7,082incl. taxes and fees

    Ideal For

    Up to 6 people

    Includes

    Private charter, catamaran

    Highlights

    Set sail on a private Caribbean charter designed around your vacation, event, preferred duration, and budget. Relax aboard a sailing yacht and celebrate any occasion on the water.

    • Customize your charter for a vacation, celebration, or special event
    • Explore Caribbean waters on a private sailing experience
    • Choose a charter duration that suits your plans
    • Celebrate an occasion with time aboard a private yacht

    Know before you go

    • Expect a fuel, dockage, and insurance surcharge not included in the listed price
    • Note that gratuity is not included
    Split the cost with your group

    This booking is for the whole experience, which fits up to 6 guests.

    From$1,180per person
    Split with

    Cancellation Policy

    Fully paid reservations are refundable less 30% with cancellation notice at least 6 months before your scheduled trip. Other refund requests are subject to management approval. Approved refunds are usually issued within 4 business days.

    FAQs

    A fuel, dockage, and insurance surcharge applies and is not included in the listed price. Gratuity is also not included; a 15% gratuity may be assessed at the completion of your charter using the card on file.

    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 #ZD2U6P

    Fits up to 6 guests

    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

    Nearby activities

    Thumbnail
    Yacht ChartersUp to 6

    4-Hour Private Cruise Charter in Key West

    $846.94
    Thumbnail
    SailingUp to 6

    3-Hour Private Sunset Sail In Key West

    From$1,634
    Thumbnail
    SailingUp to 6

    Sail & Snorkel on a 4-Hour Key West Charter

    From$1,906
    Thumbnail
    SailingUp to 6

    Sail the Florida Keys on a 12-Hour Charter

    From$3,677
    Thumbnail
    SailingUp to 6

    Key West Full-Day Private Sailing Charter

    From$2,451
    Thumbnail
    SailingUp to 6

    Private Kayak, Snorkel & Sail Charter in Key West

    $846.94