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Key West, FL

Holiday Events

Holiday Events We all know that Key West Holiday events are not only memorable, but a must do while in this destination.  We want you to celebrate these holiday events with us aboard our schooner, with a glass of Champagne in hand.

Enjoy the famous Key West Lighted Boat Parade and cruise with us through the Key West Bite.  It certainly will be a unique experience to sit aboard the Schooner America 2.0 as it joins the parade! This yacht is decked out in holiday lights for a front row seat to this historic event. 

Looking to celebrate the New Year in Key West and view the “Lowering of the Pirate Wench”?  Join us on the Schooner America 2.0 to be aboard the very yacht that lowers the Pirate Wench from its mast.  This is by far the best seat in the house and crowd free for a VIP experience. 

Furthermore, we know that seeing palm trees decorated with tinsel, and boats decorated in Holiday lights is a memorable experience. But to join us aboard the Schooner America 2.0 for one of the many Holiday events will make your stay epic.  

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 the Key West Lighted Boat Parade, a favorite maritime holiday event. Sit aboard the most elegant schooner decked out in holiday decor.  The America 2.0 will parade through the Bight and Harbor of Key West. We will be showing off our crews creative and imaginative design of twinkling lights that will dazzle all.  Up to 30 other Key West yachts will join us in the annual Key West Lighted Boat Parade. Cruise aboard America 2.0 while taking in this magical display of holiday spirit. All of the participating yachts will have the opportunity to show off their holiday decorations as they glide by the viewers and judges at the Schooner Wharf Bar. 

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $136

Key West New Year's Eve Event

New Year’s Eve Bash aboard Schooner America 2.0

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

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $246

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 us aboard Schooner America 2.0 on a Key West Valentine’s Day Sunset Sail.  This is an unforgettable sunset sail that will 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.

Our crew will cater to you as you sail through the beautiful turquoise green waters aboard 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. We will  treat you to a delicious pairing menu that is sure to entice.  The menu consists of hors d’ oeuvres expertly paired with champagnes and sparkling wines from around the world! So look no further and join us for a romantic evening on the water. 

  Duration: 2 hrs   Boat: America 2.0   Cost: $186