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    1. Local experiences
    2. /Things to do in Key West…
    3. /Celebration Packages
    4. /Engagement Packages
    5. /Key West Sunset Proposal Sail
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    Key West Sunset Proposal Sail

    Set the scene for your proposal aboard a private sunset sail

    4.8 stars• 377 reviews
    From$936/ boatincl. taxes and fees

    Duration

    2 hrs

    Includes

    Private boat, captain, crew

    Highlights

    Create a private proposal setting on the water with a captain and crew. Choose the Coral package aboard High Tide or the Pearl and Diamond packages aboard Malabar X.

    • Choose from three proposal packages with different boats and inclusions
    • Sail aboard a 35-foot vintage sailboat or 73-foot classic schooner yacht
    • Customize champagne and flower preferences for your occasion
    • Capture the moment with crew photography or a professional photographer, depending on package

    What's Included

    • Private vessel with captain and crew
    • Coolers with ice
    • Bottled water and seltzer water
    • Sparkling wine
    • Flower
    • Cupcake Sushi

    Important details

    • Arrive 15 minutes before departure for sails aboard High Tide
    • Depart from 202 Williams St. in downtown Key West for the Coral package
    • Depart from The Perry Marina, 7005 Shrimp Road, for the Pearl and Diamond packages
    • Bring sun protection and weather-appropriate clothing
    • Two weeks' notice is required for the Diamond package
    • Crew gratuity is not included in the listed price and is customary

    Cancellation Policy

    Cancel 7 or more days ahead for a full refund minus a 10% processing fee. No refund is available within 7 days. Receive a full refund if the operator cancels for any reason, including weather when they cannot rebook you.

    FAQs

    On HIGH TIDE, bring your own adult beverages and any snacks you’d like. Your sail still includes coolers with ice, bottled water, and La Croix.

    Bring sun protection and suitable weather wear (such as sunscreen, hats, and a sweater). It can feel cooler on the water, especially at sunset, so check the forecast and dress accordingly.

    No. Gratuity for the crew is not included in the price. Plan to tip at the end of your sail.

    Meeting details

    Sunset Sail Key West

    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 #X3327K

    Proposal Sail Coral Package

    $936.38

    0

    Proposal Sail Pearl Package

    $2,497

    0

    Proposal Sail Diamond Package

    $8,455.75

    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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