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Special Events

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 There are many Key West Special Events that should be experienced.  We will celebrate all of them aboard the Schooner America 2.0 so grab your pick!  

Celebrate the right way and sail Key West with us.  Enjoy a glass of Champagne in hand or your favorite beer on any of these events.  Commemorate a special occasion in grace and style aboard the Schooner America 2.0.

If you are looking for the best way to experience New Year’s Eve then join us for the epic tradition of the Lowering of The Pirate Wench.  Looking to honor your loved one then join us for our Key West Valentine’s Day Sail.  Want to join a historical maritime event then join us on the Lighted Boat Parade

We are here to help and make memories.  Our professional crew will make you feel as if you were in the comfort of your own home.  Select from one of our Key West special events and we will dazzle you with warm smiles and friendly service.  Above all, let us help you honor and celebrate the people in your lives that matter on a beautiful Key West boat ride.  


Schooner America 2.0 night sailing for a stargazing evening

Starry Night: Guided Stargazing Sail Aboard Schooner America 2.0

Join us aboard the Schooner America 2.0 after the sun goes down, setting the stage for an enchanting stargazing journey unlike any other. As the boat gently glides across the tranquil waters, your guide, a seasoned astronomer, narrates the celestial spectacle unfolding above. Pointing out constellations and tracing the mythology behind their names, they weave together tales of ancient cultures and their interpretations of the stars.

Wrapped in the darkness of the night sky, you marvel at the intricate details of distant planets, shimmering nebulae, and elusive galaxies. Each sighting is accompanied by insightful commentary from your guide, illuminating the mysteries of the universe. It’s an experience that transcends time, leaving you with memories that will twinkle brightly in your heart for years to come.

  Duration: 1.5 hras   Boat: America 2.0   Cost: General Admission $76

Stern of the schooner America 2.0 with the sails raised and the Captain Turned around waving while sailing for a Key West Wreckers Race

Wreckers Race aboard Schooner America 2.0

All hands on deck!  If you enjoy a good sailboat race, it is an absolute must for you to sail on board the Schooner America 2.0 for the Key West Schooner Wharf Bar Wrecker’s Cup Race! 

A little history…back in the days of old Key West, ships from afar often ran aground on Sand Key Reef. When all the scallywags in Key West heard there was booty to be had, they jumped in their boats and raced to the reef. The first one there could claim the ship’s cargo! Arrggh!

Today, we celebrate this Key West tradition annually with a set of monthly races from January to April. It all starts with the firing of the cannon at 1:00 PM.  Enjoy the excitement aboard Schooner America 2.0 as we race to defend our title of fastest schooner in Key West!

One round of beer, wine, champagne, and a boxed lunch are complimentary with your ticket purchase. Purchase a Beverage Package during the booking process, or additional drinks for credit card purchase while on board. (Call us directly to save 6% online processing fee)

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

Schooner America 2.0 decorated for the 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 aboard the Schooner America 2.0 with guests in the cockpit enjoying food

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

Schooner decorated in Holiday lights at a dock in key west.

Cocoa and Carols: Christmas Lights and Music Sail aboard Schooner America 2.0

Please join us for this special Key West warm and cozy holiday cruise tailored for friends, family, and all your loved ones during the Key West Christmas season. Step aboard our beautiful 105-foot Schooner America 2.0 in full holiday decor for a 1.5-hour cruise in Key West harbor while we listen to some of our favorite Christmas hits! Delicious Hot Cocoa, Cookies, and treats for all our guests are included! Sit back and enjoy this unique holiday sail in Key West on this family-friendly 1.5-hour cruise.
  Duration: 1.5 hrs   Boat: Schooner America 2.0   Cost: $56 Adults (Kids sail free)

The Schooner America 2.0 decorated for the New Year's Eve Lowering of the Pirate Wench

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

a couple being served Champagne on a 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

Family sitting in the cockpit of the Schooner America 2.0 enjoying a Mother's Day Sail in Key West FL

Momas & Mimosas: Mother’s Day Mimosa Sail aboard Schooner America 2.0

Join us on the best Key West Mother’s Day Mimosa Sail!  Take to the water on the Schooner America 2.0, namesake off the first sailboat to win the America’s Cup in 1851. This stunning 105-foot sailboat features teak decks, mahogany trimmings and ample seating. Her 3,600 square feet of sail will propel you smoothly through the crystal green waters of Key West. Guests are encouraged to make the most of the event by bringing aboard their own picnic lunch! Mom’s sail FREE! And Adults get one complimentary Mimosa or Bloody Mary.

  Duration: 1.5 hrs   Boat: Schooner America 2.0   Cost: Adults $56 | Child $24

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