Appledore Tall Ship Schooners, Sunset Sails Key West FL
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  • 205 Elizabeth Street Key West Florida 33040
  • We require a minimum of 4 hours in advance to book this activity online. Alternatively, you can contact our offices directly to inquire about short-term bookings.
  • 800-507-9955

Come aboard an Appledore tall-ship schooner and re-live maritime history. Sebago Watersports offers several Key West excursions on the historic 2-masted wooden Appledore II and the Appledore Star. Sailing a tall ship on our turquoise calm waters, you will enjoy a true sailing experience like nothing else. Choose from romantic Key West sunset sails, an afternoon schooner sail or a backcountry all-day eco adventure.

Appledore II is the largest of the original five Appledore Schooners and is considered a prime example of a historical traditional wooden schooner. Dividing her time between Camden, Maine in the summer and Key West, Florida in the winter, Appledore II sails the 2,000 miles twice a year between the two ports.

Appledore Star is the newest addition to Sebago’s wooden schooner fleet. Originally named the Jenny Norman, she was built in 1982 by legendary shipwright, Jim Richardson of Lloyds, Maryland. The last shallow-draft “bugeye schooner” known to be constructed, Appledore Star is perfect for exploring the famous Key West Backcountry.

Help hoist the sails and take a turn at the wheel on our Windjammer Classic Day Sail. Then relax and enjoy complimentary beverages while you glide across the water under full sail. Or spend a full day on the Bugeye Backcountry Eco Adventure where you’ll experience life under the sea as you snorkel and then learn about the mangrove eco-system on a guided kayak tour. This all-day adventure includes breakfast, lunch, snacks, beverages, and all equipment and instruction.

For a romantic evening, choose from two sunset sails. Our Windjammer Classic Sunset Sail and Schooner Champagne Sunset Sail both offer an intimate view of an incredible Key West sunset. The Appledore sunset sails include a selection of premium beverages, fruit, and artisanal cheeses.

For a really unique Key West sailing adventure, join Appledore II each year for the Key West Wrecker’s Cup. This regatta is held the last Sunday each month of January, February, March, and April and re-enacts the days of old when ships raced to grounded wrecks on the shallow waters’ treacherous reef.

Experience majestic tall-ship sailing for yourself on one of Sebago’s Appledore Schooners.

When You Book Direct With Sebago

Go to our website for online reservations or call us now at 800-507-9955.