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    1. Local experiences
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    5. /Stargazing Sail Charter in Key West
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    Stargazing Sail Charter in Key West

    A private evening sail with quiet stargazing beyond Key West's lights

    4.8 stars• 377 reviews
    From$675incl. taxes and fees

    Duration

    1.5 hours

    Ideal For

    Up to 6 people

    Includes

    Private boat, captain, soft drinks

    Highlights

    Sail beyond Key West's shoreline lights on a private nighttime charter. As the engine switches off, look up for seasonal celestial highlights while you cruise under sail.

    • Explore darker waters beyond the city's lights
    • Watch for seasonal celestial highlights overhead
    • Relax during a peaceful engine-off sail
    • Bring adult beverages and snacks to enjoy onboard

    What's Included

    • Private boat with captain and mate
    • Coolers stocked with ice
    • Soft drinks
    • Bottled water

    Know before you go

    • Arrive at your assigned boat's dock 15 minutes before departure
    • Children under 12 must be accompanied by an adult
    • A $75 surcharge not included in the listed price applies to each person beyond the first 6, up to 12 people total
    • Crew gratuity is customary and not included in the listed price
    • Bring weather-appropriate clothing

    Cancellation Policy

    Cancel at least 7 days before departure for a full refund minus a 10% processing fee. No refund is available within 7 days. Full refund if the operator cancels. If the captain cancels for unsafe weather and rebooking is not possible, you'll receive a full refund. No refund if you decline a trip the captain considers safe to sail.

    FAQs

    All ages are welcome. Children under 12 must be accompanied by an adult.

    A complimentary fruit platter is included. Bring any additional snacks or adult beverages you would like to enjoy.

    Experience provided by Sunset Sail Key West
    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.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #PUUHES

    Private Charter

    $675.32

    Up to 6 guests (including children)

    0

    Why book through Greetwell?

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      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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