Key West, FL

Special Events

 There are many Key West Special Events and we will celebrate all of them aboard the Schooner America 2.0!  Celebrate and sail Key West with a glass of Champagne in hand or your favorite beer!  Celebrate a special occasion in grace and style aboard the Schooner America 2.0. If you are looking to plan an adventure or excursion for New Year’s Eve join us for the 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.  We are here to help and 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 for the holiday season and let us help you honor and celebrate the people in your lives that matter on a classic Key West beautiful boat ride.  

Key West Wreckers Race

Wreckers Race aboard Schooner America 2.0

All hands on deck join us for the Key West Wreckers Race! Sail aboard the Schooner America 2.0 for the monthly Schooner Wharf Bar Wrecker’s Race! Back in the days of the yore, pirate ships from afar often ran aground on Sand Key Reef, nine miles off of the southern coast of Key West. When all the scallywags in Key West heard there was booty to be had, they’d get in their boats and race each other out to the reef. The first one there could claim the ship’s cargo! Arrggh! Today, we celebrate it with the firing of the canon at 1:00pm to start the Key West Wreckers Race, and all of the schooners of are on their way in a one-way race to Sand Key Lighthouse! The boat that gets there first, “wins”! Enjoy the excitement aboard Schooner America 2.0 as we race for victory! An awards ceremony takes place at 9 PM at Schooner Wharf Bar where the winners are announced and treasures collected.

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $75 | Child $35

Mimosa Sail aboard Schooner America 2.0

Take the helm and experience the power of this sailing machine, or sit back and relax while you sail smoothly through the crystal clear waters of Key West. Either way, it doesn’t get much better for an afternoon in Key West. This 1.5 hour sail features a complimentary mimosa bar, beer, wine, champagne and soft drinks! Bloody Marys are for purchase (credit card only)! A small hors d’oeurves plate is served, but guests are encouraged to bring aboard their own picnic lunch!

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Adult $55

Key West Classic Regatta

The Key West Classic Regatta is designed after the Great Chesapeake Bay Schooner race and is a great way to see some of the most beautiful Key West schooners in their element. It is time to jump aboard and take an adventure on Key West’s most stunning sailboat, the 105-foot Schooner America 2.0 and be a part of this annual festivity! So, all hands on deck! Join us as we push off the dock at 10:30 AM for race start! America 2.0 features beautiful teak decks, mahogany-trimmings, and with 3,600 square feet of canvas, she flys! Sit back and relax while she plies effortlessly through the crystal Green Key West sailing waters towards the finish line!

  Duration: 4.5 hrs   Boat: Schooner America 2.0   Cost: $85

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.

  Duration: 3 hrs   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.  

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $175

Quantum Key West Race Week Spectator Sail on Schooner America 2.0

Quantum Key West Race Week Spectator Sail aboard Schooner America 2.0

Join us on America 2.0, the Official Spectator Vessel for the 2017 Quantum Key West Race Week! This exciting event happens every year in these emerald green waters and you are going to have the best seat in the house.  This is a week of sailing excitement that you do not want to miss out on. Schooner America 2.0 is a 105-foot schooner that has over 3600 square feet of sail, and a cutting edge free standing carbon fiber rig!  With comfortable wrap around seating you are sure enjoy a afternoon in the sun for the Quantum Key West Race Week Spectator Sail on Schooner America 2.0!

  Duration: 4 hrs   Boat: America 2.0   Cost: Adult $75 | Child $45

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!

  Duration: 2 hrs   Boat: America 2.0   Cost: $150