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    1. Local experiences
    2. /Things to do in Key West…
    3. /Water Activities
    4. /Sailing
    5. /Key West Sunset Schooner Cruise
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    Key West Sunset Schooner Cruise

    Sail a 1930 schooner into the Key West sunset

    4.8 stars• 377 reviews
    From$123/ personincl. taxes and fees

    Duration

    2 hrs

    Includes

    Wine, beer, water & crew

    Highlights

    Sail aboard Malabar X, a 1930-built schooner designed by John G. Alden, for a shared sunset outing off Key West's Atlantic coast. Help with the sails, take the helm, or relax as the captain and crew guide the voyage.

    • Discover the history of Malabar X and her record-setting racing legacy
    • Help raise the sails or take a turn at the helm
    • Relax on a classic schooner while sailing the blue waters off the Keys
    • Enjoy a shared sailing experience with the captain and crew

    What's Included

    • Two boutique wines honoring John Alden
    • Select beers
    • Bottled water
    • La Croix sparkling water

    Important details

    • Arrive on the dock 15 minutes before departure
    • Children under 12 must be accompanied by an adult
    • Do not bring your own adult beverages
    • Expect crew gratuity to be customary and not included in the listed price

    Cancellation Policy

    Cancel 48+ hours before departure for a full refund less a 10% processing fee. No refund within 48 hours. Full refund if the operator cancels, including when weather prevents sailing and rebooking is unavailable.

    FAQs

    Arrive at the dock 15 minutes before your scheduled departure time.

    No. Guests are not permitted to bring their own adult beverages.

    Bring sun protection and suitable weatherwear (such as a hat, sunscreen, and a sweater). It can feel cooler on the water, especially after sunset.

    Meeting details

    The Perry Marina

    Experience provided by Sunset Sail Key West

    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 #CA6BS6

    Adult

    $123.72

    Ages 13+

    0

    Child

    $51.08

    Ages 3 - 12 • Must be accompanied by an adult

    0

    Infant

    $0

    Ages 2 and Under • Must be accompanied by an adult

    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
    377 reviews•Google Maps
    327
    26
    7
    3
    10

    Sailing on the historic schooner When & If is genuinely one of those experiences that surprises people. Built for General George Patton in 1939, the vessel carries real history, and the crew, led by captains like Tyler and Zack, clearly love sharing it. Guests can help raise the sails, take a turn at the wheel, or explore the crew quarters below deck. The vibe is intimate and unhurried, with no blaring music, just wind, waves, and a champagne toast as the sun goes down. The crew consistently earns high praise across the board. Veronica, Yann, Amy, and others are called out by name repeatedly for being warm, knowledgeable, and genuinely enthusiastic about the whole experience. Groups, couples, and families with young kids have all had great times, which speaks to how well the crew reads the room. One reviewer did note a dock location change that wasn't communicated when booking through a third-party platform, so it's worth confirming details directly if you're booking elsewhere. That said, it stands out as an isolated situation in an otherwise overwhelmingly positive pattern of reviews. If a sunset sail is on your Key West list, this one is hard to beat.

    What people are saying

    Review 1 of 5
    5/5

    My girlfriend and I (now fiancè) had an absolutely wonderful time on this sunset sail. Captain Bryce and Dawson were the best crew we could have imagined to get! The hors d'oeuvre's were pretty incredible. Our favorite was the smoked mahi with crustinis and cocktail shrimps! And they had my beer on tap (great choice with Bud Light btw). Dawson was extremely knowledgeable about the history of Key West and the geographical location of everything around there. Took us right to where the dolphins were to snap many videos and pictures too! The icing on the cake was right as sunset was approaching, I asked Captain Bryce if he could angle the boat for me in a way that I could have the sunset in the background as I proposed to my girlfriend. With him very recently proposing to his girlfriend (congratulations again brother) he understood the assignment. And my man Dawson after a few moments of talking, also understood the very important assignment of taking the video for us. All in all, 10/10 experience. Amazing crew, amazing food, amazing passengers too everyone on our ship was very nice. Would highly recommend to anyone looking to do a sunset sail in Key West. This is THE choice. Thanks again guys. God bless.

    Photo of Derk Diggler

    Derk Diggler

    June 22, 2026

    Review 1 of 1
    5/5

    My girlfriend and I (now fiancè) had an absolutely wonderful time on this sunset sail. Captain Bryce and Dawson were the best crew we could have imagined to get! The hors d'oeuvre's were pretty incredible. Our favorite was the smoked mahi with crustinis and cocktail shrimps! And they had my beer on tap (great choice with Bud Light btw). Dawson was extremely knowledgeable about the history of Key West and the geographical location of everything around there. Took us right to where the dolphins were to snap many videos and pictures too! The icing on the cake was right as sunset was approaching, I asked Captain Bryce if he could angle the boat for me in a way that I could have the sunset in the background as I proposed to my girlfriend. With him very recently proposing to his girlfriend (congratulations again brother) he understood the assignment. And my man Dawson after a few moments of talking, also understood the very important assignment of taking the video for us. All in all, 10/10 experience. Amazing crew, amazing food, amazing passengers too everyone on our ship was very nice. Would highly recommend to anyone looking to do a sunset sail in Key West. This is THE choice. Thanks again guys. God bless.

    Photo of Derk Diggler

    Derk Diggler

    June 22, 2026

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