easy
4–6 hours
Suitable for all fitness levels as the sailing is relaxed with opportunities to rest on deck.
Set sail aboard the historic Appledore Star for a private day adventure exploring Key West's iconic waters. Enjoy snorkeling, sunbathing, and expert sailing in an unforgettable Florida Keys experience.
Starting at $49.95 per Adult | 2 Hours
Private Charters starting at just $995!
2 Hours
Experience sailing on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger windjammer. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.
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 cocktail of your choice including homemade sangria, boutique wine, frosty cold premium beers, soft drinks and water. A full bar is also available.
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.
With the Historic Seaport drawing closer, your schooner sail cruise is nearing its end. Life is good in paradise.
Protect your skin and marine life by using reef-safe sunscreen during your sail.
Bring a reusable water bottle to stay hydrated throughout the day on the water.
Choose non-slip footwear to stay safe while moving around the wet deck.
Evenings on the water can get breezy, so a light jacket will keep you comfortable.
Key West has a rich maritime history, once serving as a strategic naval base and thriving fishing port dating back to the 19th century.
Appledore promotes eco-friendly sailing practices to protect coral reefs and marine habitats in the Florida Keys National Marine Sanctuary.
Protects your skin and the delicate marine ecosystem during sunny sailing days.
summer specific
Reduces glare from water making it easier to spot marine life and navigate.
Ideal for swimming or snorkeling when the boat anchors in calm bays.
summer specific
Useful in cooler breezes, especially during early morning or late afternoon sails.
spring specific