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    5. /Key West Tall Ship Sailing Cruise
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    Key West Tall Ship Sailing Cruise

    Hoist sails and take the wheel aboard a 2-masted schooner

    4.9 stars• 3K reviews

    Includes

    Sailing, drinks, cocktails

    Highlights

    Explore the Atlantic aboard Appledore II, a 2-masted schooner that pairs traditional tall-ship sailing with the comforts of a modern passenger windjammer. Leave Key West's Historic Seaport behind as you sail in tropical salt air.

    • Help raise the sails alongside the crew
    • Take a turn at the wheel of a traditional tall ship
    • Sail past Key West Harbor, Mallory Square, Sunset Key, and Fort Zachary Taylor
    • Watch for dolphins, turtles, ospreys, and pelicans

    What's Included

    • Homemade sangria
    • Boutique wine
    • Premium beer
    • Cocktails
    • Soft drinks and water

    Important details

    • Children under 18 must be accompanied by an adult
    • Bring a valid government-issued photo ID to consume alcohol

    Cancellation Policy

    Cancel 48 hours or more before departure for a full refund or to rebook, subject to availability. Cancellations less than 48 hours before departure are not eligible for a refund. If the tour is cancelled due to the captain's discretion or weather, receive a full refund or rebook, subject to availability.

    Product ID: UGKSZX

    FAQs

    Check in 30 minutes before departure. Every member of your party must be present to sign a waiver and receive a boarding pass.

    Yes. For the Windjammer Classic Day Sail, a 15–20% tip is customary.

    Meeting details

    Schooner Appledore Check-In Booth, 200 William Street, Key West, FL 33040

    Experience provided by Appledore - 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

    Adult

    $56.70

    Ages 12+

    0

    Child

    $34

    Ages 4-11

    0

    Young Child

    $0

    Ages 3 & Under

    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

    4.9
    Excellent
    3K reviews•Google Maps
    2,854
    65
    20
    11
    20

    The schooner draws near-universal praise, and it's easy to see why. Captains and crew, including frequently mentioned Joe, Christina, and Marison, consistently earn compliments for being professional, knowledgeable, and genuinely fun to spend a day with. The boat itself is described as beautiful and immaculately maintained, adding to an overall sense that this operation takes real pride in what they do. The two main offerings, a sunset sail and a daytime ecotour with snorkeling and kayaking, both deliver strong experiences, though in different ways. The sunset cruise focuses on the magic of being out on the water with drinks flowing and appetizers to snack on, while the ecotour leans into wildlife encounters and mangrove exploration. Dolphins, sea turtles, and even the occasional shark have made appearances on multiple trips, which travelers clearly love. Food and drinks are included and repeatedly praised, which seems to be a pleasant surprise for many guests. With a near-perfect rating across thousands of reviews, this is about as close to a sure thing as you'll find in Key West. Booking early makes sense, especially during busy seasons.

    What people are saying

    Review 1 of 4
    5/5

    My wife and I did the sunset cruise years ago and loved it. We are back in the Keys this week with 5 other family members and booked it for last evening. Everyone had a great time. Worth doing every time we visit.

    Photo of Michael Vance

    Michael Vance

    September 3, 2026

    Review 1 of 1
    5/5

    My wife and I did the sunset cruise years ago and loved it. We are back in the Keys this week with 5 other family members and booked it for last evening. Everyone had a great time. Worth doing every time we visit.

    Photo of Michael Vance

    Michael Vance

    September 3, 2026

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