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

    Charter a 1939 wooden schooner for a sunset sail from Key West’s Historic Seaport

    4.8 stars• 373 reviews
    From$2,474incl. taxes and fees

    Duration

    2 hours

    Ideal For

    Up to 6 people

    Includes

    Captain and crew, Drinks

    Highlights

    Step aboard a classic 1939 wooden schooner and take in Key West at sunset on a private 2-hour sail. Pitch in to raise sail or take the helm, or settle back and enjoy the ride.

    • Depart from and return to the end of E Dock at the historic Key West Seaport
    • Sail with a captain and crew on a private charter
    • Help raise sail and take a turn at the helm
    • Watch sunset views from the water
    • Choose optional extras like more sailing time, catering, or custom pick-up and drop-off locations

    What's Included

    • Private use of the vessel
    • Captain and crew
    • Wine
    • Select beers
    • Champagne
    • Bottled water
    • Seltzer water

    Things to know

    Gratuity for the crew is not included; clarify the amount with Greetwell before booking. Guests are not permitted to bring their own adult beverages. Some sail dates may coincide with a reenactment that can include loud cannon fire and water cannons.

    Cancellation Policy

    Private charters: cancel 7+ days in advance for a full refund minus a 10% processing fee. No refund within 7 days. If the operator cancels for any reason, you get a full refund. If the captain cancels due to weather and you can’t rebook, you get a full refund.

    FAQs

    Bring suitable weather wear (sunscreen, hat, sweater), plus adequate sun protection. You can also bring any snacks you’d like. It can feel cooler on the water, especially in the breeze and at sunset in winter, so dress for conditions.

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

    No. Gratuity for the crew is not included, but it is customary and appreciated; plan to tip at the end of your sail.

    Experience provided by Sunset Sail Key West
    Experience provided by Sunset Sail Key West

    Related locations

    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 #RZEYDT

    Private Charter

    $2,474.30

    Up to 6 guests (including children)

    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
    373 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

    This is the BEST thing to do in Key West! I'm typically not a fan of the usual tourist fare, but a sunset cruise is always a quick yes when my wife asks. I had no idea that I would be sailing on a historically significant schooner, manned by a three person crew who actually live aboard. You can go below and see the crew quarters, galley, the inner workings, help hoist the sail (I wanted to but my elbows are shot) or even steer the vessel. Captain Tyler and the crew know many of the Captains on the other boats. Expect cannon and musket fire! (I did get to fire the cannon). I also learned the term Shooner Eclipse....hysterical. I would also point out that EVERY negative review I found on their Google reviews was for a different business on the same dock. Thank you Captain Tyler, JP and Veronica. Best cruise ever!

    Photo of michael mcmullen

    michael mcmullen

    May 19, 2026

    Review 1 of 1
    5/5

    This is the BEST thing to do in Key West! I'm typically not a fan of the usual tourist fare, but a sunset cruise is always a quick yes when my wife asks. I had no idea that I would be sailing on a historically significant schooner, manned by a three person crew who actually live aboard. You can go below and see the crew quarters, galley, the inner workings, help hoist the sail (I wanted to but my elbows are shot) or even steer the vessel. Captain Tyler and the crew know many of the Captains on the other boats. Expect cannon and musket fire! (I did get to fire the cannon). I also learned the term Shooner Eclipse....hysterical. I would also point out that EVERY negative review I found on their Google reviews was for a different business on the same dock. Thank you Captain Tyler, JP and Veronica. Best cruise ever!

    Photo of michael mcmullen

    michael mcmullen

    May 19, 2026

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