Special Events

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)

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)

Easter Brunch Sail aboard Schooner America 2.0

Enjoy your Easter morning aboard Key West’s most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West as you sip champagne, dine on passed a delicious brunch, and glide through the crystal clear surrounding waters. This two-hour day sail features complimentary mimosas, Bloody Marys, champagne, wine, beer, soft drinks, and water. Brunch is provided, including spiraled ham, bagels and pastries, meats and cheeses, smoked salmon, crudite, and other delicious treats! Schooner America 2.0 is a state of the art vessel built in 2011. She features teak decks, mahogany-trimmings, and 3600 square feet of canvas! Sit back and relax while she plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West sailing experience!

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. (Call us directly to save 6% online processing fee)

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. (Call us directly to save 6% online processing fee)

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)