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Windjammer Classic Day Sail

A historic sail with a modern day twist.
Experience sailing on a majestic 2-masted schooner.

Enjoy a swashbuckling adventure straight out of the 19th century, but with modern, luxurious state-of-the-art accommodations aboard this sleek windjammer. And because we limit capacity to just 49 passengers, look forward to a uniquely intimate experience.

The Appledore II is the second in a series of historic schooners designed to travel the world. She winters in Key West, taking our guests on unforgettable excursions. During your sail, as the crew begins to hoist the sails, jump in and participate in this age-old maritime tradition. Then, take your turn at the helm and feel the exhilaration of captaining a traditional tall ship.

Appledore II is a true working ship, sailing year-round. When not in Key West, she spends her summers sailing around Camden, Maine. It’s a 2,000 mile ocean voyage she makes twice a year between her homeports. Some of your crewmembers have made this voyage with her, ask them about their adventures!

Sails unfurled, billowing in the wind, you’ll soon find the Historic Seaport in your wake as you head into the open waters of the Atlantic. With the wind in your hair and the salt air on your face, you’ll glide past Key West’s Harbor, Mallory Square, the Navy Mole, Sunset Key and historic Fort Zachary Taylor.

Out to sea, keep your eyes open and your head on a swivel. We all know there is abundant marine life under the water, but there is also plenty to see on the water’s surface or circling above in the blue sky. A pod of dolphins may surface or you might spot a turtle floating by; perhaps an osprey will swoop down to catch its lunch; or a pelican will make a splash down off the starboard side.

Throughout your afternoon adventure, sip on complimentary beverages including homemade sangria, boutique wine, ice-cold premium beers, a full bar, soft drinks and water.

Then, when the Historic Seaport comes into view and your schooner cruise nears its end, you’ll find yourself full of stories and memories to last a lifetime. Life is good in paradise; life is good in Key West.

You will be sailing on Sebago's Appledore II, a two-masted 86' windjammer featuring:

  • Wide decks with plenty of room to walk around
  • Generous seating options
  • A limit of 49 passengers for an intimate sail
  • A spacious head (bathroom)

Departs daily at 1:30pm with boarding starting at 1:00pm.

Tour includes:

  • Take part in hoisting the sails and a turn at the wheel
  • Homemade sangria, boutique wine, premium beer, full bar, soft drinks and filtered water

What To Bring

Grab your hat, sunglasses, camera and love of adventure. We do the rest! Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age.



Smiling Girl
AGES 4-11:


Baby Boy

No Charge


2 Hours



Boarding Starts 1/2 Hour Before. Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age. All prices do not include Florida sales tax.

Tour Includes:

  • Sail Past Local Key West Landmarks
  • Take Part in Hoisting the Sails and a Turn at the Wheel
  • Home-made Sangria, Boutique Wine, Premium Beer, Full Cocktail Bar, Soft Drinks and Filtered Water