Special Events in Key West - Sailing Key West, things to do in Key West, FL

Holidays and Special Events

 

Key West Lighted Boat Parade

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Join us for Key West's 20th annual Lighted Boat Parade, a favorite maritime holiday event. Sit aboard the most stunning Schooner America 2.0, as we parade through the Bight and Harbor of Key West decorated in Holiday decor with up to 30 other Key West vessels. Cruise aboardAdirondack III while taking in this magical display of holiday spirit.

New Year's Eve lowering of the Wench aboard America 2.0

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Join us this New Year's Eve in Key West! America 2.0 will be the Schooner that the famous lowering of the Wench will take place!  Watch in anticipation and awe as the Wench gets lowered from this 85 foot high mast!

Civil War Heritage Day Sea Battle on America 2.0

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The 28th Annual Civil War Heritage Days features a sea battle with schooners, re-en actors dressed in period costumes, demonstrations. Come south and enjoy crafts from the Civil War era and experience a land and sea battle.  This event that will have you experiencing life in the Florida Keys as it was back in the mid 1800’s.  Fort Taylor was the guardian of the shipping lanes to ports on the Gulf of Mexico.  The Fort was placed under a blockade by President Lincoln in 1861. Blockade runners captured by Union navy vessels were forced to anchor in front of the fort as captured “war prizes.” Federal and CSA troops will have an opportunity to be aboard authentic 1860s schooners in Key West Harbor to engage in battle.

Key West Valentines Day Sails!

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Join us on any of our Romantic Key West Sail aboard Schooner America 2.0 or Yacht Beacon.  Create a memory of a life time this Valentine's Day! Treat yourself and your loved one to a sunset sail or day sail. Each of these cruises are specially designed for Valentine's Day!  Check our online calendar for the sails on February 14th!  Chocolate, Roses, Strawberries and more!

Wreckers Race Sail aboard Schooner America 2.0

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All hands on deck! Join us for the monthly tradion in Key West: the Wreckers Race! Sail aboard the Schooner America 2.0! Back in the day of the ole pirates, ships from afar used to run aground on Sand Key Reef. Then all the scallywags in Key West would get in their boats and race out to the reef! The first one there could claim the ship's cargo!

Key West's Full Moon Sail Aboard Schooner America 2.0

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Take to the Key West waters by Full Moon Light!! This monthly romantic, moonlight sailing adventure is yours aboard Key West's most stunning sailboat, the 105-foot schooner, America 2.0. Sit back and relax while she slices through the evening, basking in the golden moonlight that dances in the night waters.

Key West Classic Regatta

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Join us for this brand new annual tradition and sail aboard the fastest and most elegant schooner in the local Key West fleet:America 2.0. The Key West Classic Regatta is desiged after the Great Chesapeake Bay Schooner race and will draw beautiful vessels together to partake in this sailing adventure.