Day Sailing

Classic Day Sail aboard Schooner America 2.0

It is true! When in Key West you must soak in the sun while you do some classic Key West day sailing. We think the best way to spend an afternoon is to take to the water on the Schooner America 2.0 for a Key West Day Sail! Named after the first boat to win the America’s Cup in 1851. Our stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating. There is over 3,600 square feet of sail that will propel you smoothly through the crystal green waters of Key West. We boast a full bar on board which is available for credit card purchase. Soda and water are complimentary. Guests are encouraged to bring aboard their own picnic lunch!

Key West Mimosa Sail on Schooner America 2.0

Good Morning Mimosa Lovers! Step aboard for a Key West Mimosa Sail on our stunning Schooner America 2.0! Start your day off right and take the helm and experience the power of this sailing machine.  Or sit back and relax while with a mimosa in hand as you sail smoothly through the crystal clear waters of Key West. Either way and above all, it doesn’t get much better for an afternoon day sail 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!

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!

Beer, wine, champagne, and a boxed lunch are complimentary with your ticket purchase.

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!

Christmas Day Brunch Sail aboard Schooner America 2.0

Enjoy your Christmas Day 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 ona 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 includes spiraled ham, bagels and pastries, meats and cheeses, smoked salmon, crudite, and other delicious treats!

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!