Windjammer Classic Day Sail

Windjammer Classic Day Sail

Featuring the Commodore’s famous Bloody Mary’s

Experience sailing on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious accommodations of a traditional passenger windjammer.

The Appledore II is the second in a series of historic schooners commissioned by the Smith family to travel the world. Feel the sense of adventure as the crew hoists the sails. Participate in the age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of being at the helm of a traditional tall ship.

Appledore II is no pampered ship, she sails year-round. Summers are spent sailing around Camden, Maine and winters are here in tropical Key West. Twice a year Appledore II sails the 2,000 mile ocean voyage between her two homeports. Some of the crew on your tour have made this exciting journey – ask them about their adventures.

Sails flying in the wind, you leave behind the Historic Seaport and head out to the Atlantic. Soon there is wind in your hair and the warm, tropical salt air kisses your face. Take in the view as the schooner navigates her way past Key West’s Harbor, Mallory Square, the Navy Mole, Sunset Key and historic Fort Zachary Taylor.

Quench your thirst with complimentary homemade sangria, boutique wine, frosty cold premium beers, full cocktail bar, soft drinks and water.

While there is abundant marine life under the water, there is also plenty to see on the water’s surface or circling in the blue sky above you. A pod of dolphins may surface or you might spot a turtle floating by. Perhaps an osprey will plummet down to the water to catch its lunch or a pelican will make a splash landing near the vessel.





Wide decks with room to walk around

The Commodore’s famous Bloody Mary’s!

Generous seating

Up to 49 passengers for an intimate sail

A spacious head (bathroom)


What To Bring

Grab your hat, sunglasses, camera and love of adventure. We will do the rest!

Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age.


Welcome back!  We are pleased to announce our official re-opening on June 5th with reduced capacities and additional safety protocols to ensure a safe and enjoyable experience for both passengers and crew.  Advanced reservations (book Online or Call) are required. No walk ups are permitted per the City of Key West at this time.