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Key West, FL

Holiday Events

Holiday Events Key West Holiday events  are not only memorable but a must do while in this beautiful vacation destination.  We want to celebrate these holiday events with you with a glass of Champagne in hand aboard a classic yacht. Enjoy the famous Key West Lighted Boat Parade and cruise through the bite aboard our well decorated sailing boat.  Looking to celebrate The New Year and view the Lowering of the Pirate Wench?  Step aboard the Schooner America 2.0 and be aboard the very yacht that lowers the Pirate Wench from the mast of a 105 foot schooner!  Palm trees decorated with tinsel, and boats decorated in Holiday lights. Join us in Key West aboard the Schooner America 2.0 for one of the many Holiday activities that we celebrate.  Are you just in town for the weekend? Then join us on a Key West day sail or the romantic Key West sunset sail to catch a glimpse of the “Green Flash”. Whichever you choose, you will be sure to have a good old Key West time! 


Key West Lighted Boat Parade

Lighted Boat Parade aboard Schooner America 2.0

Join us for Key West Lighted Boat Parade, a favorite maritime holiday event. Sit aboard the fastest, most elegant schooner, the brand new eco-friendly, America 2.0 as we parade through the Bight and Harbor of Key West!  She’ll be fully decorated in Holiday decor with up to 30 other Key West vessels in the annual Key West Lighted Boat Parade. Cruise aboard America 2.0 while taking in this magical display of holiday spirit. All of these vessels will have the opportunity to show off their creative and imaginative holiday decorations as they glide by the viewers and judges at the Schooner Wharf Bar.

  Depart: Schooner Wharf   Boat: America 2.0   Cost: Adult $85 | Child $45

Key West New Year's Eve Event

New Year’s Eve Bash aboard Schooner America 2.0

Join us aboard America 2.0 for a wonderful New Year’s Eve Bash! This Key West New Year’s Eve Event aboard the Schooner America 2.0 is one that must not be missed.  Enjoy this timeless celebration on the most exclusive boat in the Historic Bight, and experience VIP dockside access to the famous Schooner Wharf Bar “Lowering of the Pirate Wench” from the rig of Schooner America 2.0! This special ’21 and older’ event features complimentary beer, wine, champagne, well drinks, soda, water, and delicious hors d’ oeuvres! The Key West New Year’s Eve Event will separate you from the crowds and give you the best seat in the house for a front row viewing of the Lowering of the Pirate Wench.  

  Depart: Schooner Wharf   Boat: America 2.0   Cost: Adult $165

Key West Valentine's Day Sunset Sail

Champagne & Aphrodisiacs Valentine’s Day Sail

This Valentine’s Day, take to the water and fall in love all over again. Join Schooner America 2.0 on a Key West Valentine’s Day Sunset Sail for an unforgettable sunset that is sure to tickle your taste buds and create a memory to last a lifetime. Celebrate this Valentine’s Day with your special someone on our Champagne and Aphrodisiacs Pairing Sunset Sail in Key West. As you sail along the beautiful turquoise green waters on the Schooner America 2.0, you and your loved one will be able to take in all the romance that this Key West Valentine’s Day Sunset Sail has to offer while being treated to a delicious pairing menu that is sure to entice consisting of hors d’ oeuvres expertly paired with champagnes and sparkling wines from around the world!

  Depart: Schooner Wharf   Boat: America 2.0   Cost: Price Varies $85 - $125