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Key West Holiday Events

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Holiday Events We have many Key West Holiday Events that are perfect for you. The holidays are a magical time in Key West, and we want you to spend yours with us aboard the Schooner America 2.0 with a glass of Champagne in hand! 

Our Key West Holiday Events are annual and happen every Christmas season.  Enjoy the famous Key West Lighted Boat Parade and cruise aboard the Schooner America 2.0 as it joins the parade decked out in holiday lights.  We’ll have a front row seat to this historic event! 

What better way to celebrate Christmas morning than aboard the Schooner America 2.0!   Join us for a Key West Christmas day brunch cruise where you’ll enjoy a fully-catered brunch and delicious mimosa! 

Looking to celebrate the New Year in Key West? What better way than to watch the Schooner Wharf Bar Annual Lowering of the Pirate Wench?This is the best Key West New Year’s Eve party in town!  The Schooner America 2.0 is the very yacht that lowers the Pirate Wench from its mast! This is by far the best place to be for a VIP experience. In addition this is a intimate setting away from the crowded docks. 

And of course, you can always join us for 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! 


Schooner America 2.0 sailing in the night for a Full Moon Sail!

Full Moon Sail Aboard Schooner America 2.0

Sail through the Key West waters by full moonlight on this romantic Full Moon sailing adventure aboard one of Key West’s most stunning modern sailboats, the 105 ft Schooner America 2.0. This special sail is only offered for a limited time every month! Ticket price includes 1.5 hours of sailing, two alcoholic beverages, complimentary soft drinks, and water. Pro Tip: Call us directly to avoid the 6% online processing fee.

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Adult $64 | Child $36

New Year’s Eve Dockside 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 Dockside New Year’s Eve Bash! Your ticket grants you VIP dockside access to the famous Schooner Wharf Bar “Lowering of the Pirate Wench” as we lower her from the rig of our very own Schooner America 2.0! 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 all night! (Call us directly to save 6% online processing fee) 

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

Key West Valentine's Day Sunset Sail

Champagne Sunset Valentine’s Day Sail

Join us for our Key West Valentine’s Day Sunset Sail aboard the Schooner America 2.0!  This is a day to celebrate your loved one.  So spend Valentine’s Day in Key West aboard our elegant Schooner. It truly is the perfect way to show your love and appreciation. Sail through Key West with a glass flute of French champagne in hand and cruise aboard our classic boat for an evening of elegance.  Watch the sun dip beyond the horizon.  Snuggle up with your loved one to celebrate your love for each other.  Reflect on your relationship aboard this Valentine’s Day cruise.Our professional crew will cater to your every need. We will wine and dine you and make you feel like royalty. Key West sailing is a magical way to capture a moment in time.  So what better cruise to do this on then the Key West Valentine’s Day Sunset Sail.  This magical Key West sunset sail will take your breath away and your loved one will be swept off their feet all over again. (Call us directly to save 6% online processing fee)

  Duration: 2 hrs   Boat: America 2.0   Cost: $136

Key West Lighted Boat Parade

Lighted Boat Parade aboard Schooner America 2.0

Join us for the Schooner Wharf Bar Annual 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 crew’s creative design of twinkling lights that will dazzle all! (Call us directly to save 6% online processing fee) 

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $104

Key West Brunch Sail

Christmas Day Brunch Sail aboard Schooner America 2.0

Are you dreaming of a crystal clear, blue Christmas? Then, spend your Christmas morning aboard the Schooner America 2.0 for a brunch sail that you and your loved ones will never forget! Start your day with complimentary mimosas, bloody mary’s, or champagne as you sail into the Christmas spirit. This two-hour sail includes a fully-catered brunch that will be sure to help you start Christmas day the right way! On this peaceful holiday sail, you can relax to the natural sounds of the wind and waves, and appreciate the beauty of Key West during the holiday season. (Call us directly to save 6% online processing fee)

  Duration: 2.5 hrs   Boat: Schooner America 2.0   Cost: Adult $136 | Child $63

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