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Key West, FL

Sail Racing

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Besides being known for great food and music, Key West is also known for its perfect sailing conditions. And what better way to experience sailing than aboard the Schooner America 2.0 for a race! 

Unlike most traditional schooners, Schooner America 2.0 was built for both speed and comfort. We would love for you to experience our her grace and style, and our crew’s incredible service at one of our annual race events.

Our stunning, black-hulled, 105-foot sailing yacht is a tribute to the first Schooner America, the namesake and winner of the first America’s Cup in 1851. And true to her predecessor, Schooner America 2.0 has won over 30 races in the past 8 years! 

So grab your tickets! A sailing race is something that you must experience while staying in Key West!


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!

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

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $96

Key West Wreckers Race

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