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

    Sail Key West aboard a 1939 wooden schooner built for General George S. Patton

    4.8 stars• 376 reviews

    Duration

    2 hrs

    Includes

    Captain and crew, wine and beer

    Highlights

    Step aboard When And If, a 1939 wooden schooner built for General George S. Patton, for a shared sail with a captain and crew. Help raise the sails, take a turn at the helm, or relax as you take in Key West from the water.

    • Help raise the sails aboard a historic wooden schooner
    • Take a turn at the helm with the crew
    • Enjoy Key West sights and sounds from the water

    What's Included

    • Captain and two crew members
    • Two boutique wines made in honor of the yacht
    • Select beers
    • Bottled water and seltzer water

    Important details

    • Arrive 15 minutes before departure
    • Ages 3+ only; children ages 3–12 must be accompanied by an adult
    • Florida Keys Local rate requires proof of home address at entrance
    • Outside adult beverages are not permitted
    • The captain determines whether conditions are safe to sail

    Cancellation Policy

    Cancel at least 48 hours before departure for a full refund minus a 10% processing fee. No refund for cancellations within 48 hours. Full refund if the operator cancels, including when weather prevents sailing.

    Product ID: DG9T5X

    FAQs

    The shared sail requires a minimum of 8 people to sail.

    Bring weather-appropriate layers, sunscreen, and a hat. Check the forecast; you may also want a dry bag, change of clothes, and foul-weather gear for the historic schooner sail.

    Gratuity for the captain and crew is not included in the listed price. It is customary and appreciated at the end of your sail.

    Meeting details

    The Perry Marina, 7005 Shrimp Road, Key West, FL 33040

    Experience provided by Sunset Sail Key West

    Related locations

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

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    Report an issue

    Adult

    $85.12

    Ages 13+

    0

    Child

    $44.26

    Ages 3 - 12 • Must be accompanied by an adult

    0

    Florida Keys Local

    $68.10

    Proof of home address will be required at entrance.

    0

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      No booking or service fees, ever

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      Most experiences can be cancelled for a full refund

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    Review summary

    4.8
    Excellent
    376 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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