Key West Schooner Sailing

Take to the sea aboard an 1890s-style schooner from Key West! As you sail through the turquoise waters, enjoy views of Key West sights like Fort Zachary Taylor, Mallory Square, Sunset Pier and Sand Key Light Tower. You have two sailing options – sail on the most stunning sailing vessel with wine and soft drinks for $1 each, or on the newest sailing vessel with an open bar of beer, wine and soft drinks.

Admire the beauty of Key West from a sailboat on the clear, calm Caribbean waters. Step back in time aboard one of two 1890s-style schooners – the Adirondack III or America 2.0. Your US Coast Guard-certified captain will hug the pristine coastline, providing you with amazing views of Key West sights like Fort Zachary Taylor, Mallory Square, Sunset Pier and Sand Key Light Tower.

Both sailing options are 90 minutes long and have a bar on board. You are encouraged to bring your own snacks or picnic lunch to enjoy on the schooner!

Adirondack III
As one most stunning sailing vessels in Key West, the 80-foot (24 meters) wooden pilot schooner, Adirondack III, has been entertaining passengers for several years. Relax on the beautiful teak and mahogany decks and admire the authentic finishes as you enjoy the sea breeze and sip on a drink. The Adirondack III has a bar with beer, wine and soft drinks for just $1 each. 

America 2.0
Enjoy a premier sailing experience aboard the winner of the 2011 Great Chesapeake Bay Schooner Race – the America 2.0.  This stunning 105-foot (30 meter) boat features teak decks, mahogany trimmings and padded bench seating. Her 3,600 square feet (334 square meters) of sail will propel you smoothly through the crystal blue waters of Key West. On board, make your way to the open bar for complimentary beer, wine and soft drinks for the duration of the sail. 

Schedule details

Schooner Replica

Departure Dates:

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Departure Point:

Departure Time:

Adirondack III: Daily
America 2.0:  Seasonal November - April

Return Details:

Pricing information

Click the link below to check pricing & availability on your preferred travel date. Our pricing is constantly updated to ensure you always receive the lowest price possible.

Tour options:

Additional information

America 2.0

Inclusions:

• 1.5-hour coastal sailing tour 
• Open bar with beer, wine and soft drinks (if option selected)

Exclusions:

• Gratuities (optional)
• Hotel pickup and drop-off
• Garage parking
• Food and drinks, unless specified

Additional Information:

• Confirmation will be received at time of booking, unless booked within 1 day of travel. In this case confirmation will be received as soon as possible, subject to availability
• Operates in all weather conditions unless unsafe, please dress appropriately
• All sales are final

Voucher Info:

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Local Operator Information:

Complete Operator information, including local telephone numbers at your destination, are included on your Confirmation Voucher. Our Product Managers select only the most experienced and reliable operators in each destination, removing the guesswork for you, and ensuring your peace of mind.