Sail Key West’s historic waterfront aboard a hand-built 86-foot schooner
Drinks, hors d'oeuvres, shrimp
Step aboard Appledore II, an 86-foot, two-masted wooden schooner built in the tradition of 1800s schooners. Sail into the Atlantic off Key West as the crew hoists the sails, with opportunities to help raise them and take a turn at the wheel.
Pass the Key West Historic Seaport, Mallory Square’s Sunset Celebration, the Navy Mole, and Fort Zachary Taylor as the captain positions the ship for sunset views.
Cancel at least 48 hours before departure for a full refund. Cancellations less than 48 hours before departure are nonrefundable. Receive a full refund if the captain cancels due to weather or at the captain's discretion.
Product ID: FM2A3N
Arrive 30 minutes before departure. Every member of your party must be present at check-in to sign a waiver and receive a boarding pass.
Bring a valid government-issued photo ID to consume alcohol on the sunset sail.
Children under 18 must be accompanied by an adult.
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.
Light up the sea floor on a guided kayak paddle beneath the stars
Climb 88 steps for panoramic island views and explore the Keeper’s Quarters Museum
Cruise to a Key West sandbar for swimming, relaxing, and wildlife watching
Reef fishing for snapper and grouper, with bait and tackle included
Set your own pace at remote Key West sandbars and beaches
Parasail above Key West on a 12-passenger boat with tandem flight options