Hoist sails and take the wheel aboard a 2-masted schooner
Sailing, drinks, cocktails
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.
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
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.
Schooner Appledore Check-In Booth, 200 William Street, Key West, FL 33040
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.
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.
Michael Vance
September 3, 2026
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.
Michael Vance
September 3, 2026
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