Key West, FL

Day Sailing


Join us for a Key West Day Sail, an afternoon sailing trip, or a sightseeing boat tour on the sailboat America 2.0. Cruise through the waters of Key West aboard this luxury yacht and sail with the dolphins. Depending on the weather conditions we will head out to Fleming Key, Sunset Key, Sand Key Light House or Fort Zachary Taylor to catch a glimpse of these stunning animals as they surf along the bow of our boat.  Soak in the sun and enjoy a afternoon on the water in Key West with friends and family aboard this beautiful schooner. Cruise through the emerald green water for a Key West day sail with a glass of Champagne in hand, wind in your hair and your feet kicked up!  

Sailing aboard a classic boat in Key West is a must do water activity while on your stay. The Schooner America 2.0 will dazzle you and give you the most premium sailing experience Key West has to offer.  If you are not interested in a Day Sail then join us on the best Key West Sunset Sail in town! 

Key West Day Sailing

Classic Day Sail aboard Schooner America 2.0

Soak in the sun while you do some Key West Day Sailing!  Take to the water on the Schooner America 2.0, named for the first boat to win the America’s Cup in 1851 for some Key West day sailing. This stunning 105-foot boat 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 Florida. This 1.5 hour Key West day sail features complimentary beer, wine, champagne and soft drinks! Refreshing fresh fruit is provided, but guests are encouraged to make the most of the event by bringing aboard their own picnic lunch!

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Adult $55 | Child $35

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

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

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