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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 Key West’s Atlantic coast at sunset aboard a historic schooner

    4.8 stars• 376 reviews

    Duration

    2 hrs

    Ideal For

    Up to 32 people

    Includes

    Captain and crew, wine, beer

    Highlights

    Step aboard the schooner When and If, the custom-built yacht once owned by General George S. Patton and preserved for continued sailing. Share an evening on the water off Key West’s Atlantic coast as the captain and crew take you out to catch the breeze.

    Help raise a sail, take a turn at the helm, or relax aboard this classic yacht as the sun goes down.

    • Discover the story of General Patton’s custom-built schooner
    • Help raise sail or take a turn at the helm
    • Enjoy blue-water sailing off the Keys’ Atlantic coast

    What's Included

    • Sailing with the captain and crew aboard the schooner When and If
    • Two boutique wines made in honor of the boat
    • Select beers
    • Bottled water
    • La Croix sparkling water

    Important details

    • Arrive at the dock 15 minutes before departure
    • Children under 12 must be accompanied by an adult
    • Outside adult beverages are not permitted
    • Crew gratuity is customary and not included in the listed price

    Cancellation Policy

    Cancel 48+ hours before departure for a full refund minus a 10% processing fee. No refund within 48 hours. Rescheduled trips are not eligible for compensation. Full refund if the operator cancels, including when weather prevents sailing. No refund if you choose not to sail when the captain deems conditions safe.

    Product ID: 2C2U78

    FAQs

    Bring sun protection and weather-appropriate layers. It can be cooler on the water after sunset; you may also wish to bring a dry bag, change of clothes, and foul-weather gear.

    Meeting details

    End of E Dock, Key West Historic Seaport, 202 William St

    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

    Adult

    $123.72

    Ages 13+

    0

    Child

    $51.08

    Ages 3 - 12 • 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
    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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