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

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

Key West Sunset Sail

Key West Sunset Sail on Schooner America 2.0

Enjoy the best sunset sail in Key West on the Schooner America 2.0!  Take in the vibrant colors of Key West’s famous sunset as you sip complimentary champagne.  On this Key West Sunset Cruise you will magically glide through the crystal clear surrounding waters whilst being taken care of by our professional and friendly crew.

This two-hour Key West sunset cruise features complimentary champagne, wine, beer, soft drinks, and water. Guests are encouraged to bring their own picnic! Sit back and relax while Schooner America 2.0 plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West Sunset experience! (Call us directly to save 6% online processing fee)

  Duration: 2 hrs   Boat: America 2.0   Cost: Adult $96