Key West

Florida

Classic Harbor Line Key West offers a wide variety of sailing trips from half-day excursions to overnight voyages. Each sailing trip has been designed to give you quality time on the water with friends or family while exploring some of Florida's most beautiful waterways. Whether you're looking for an adrenaline rush, a relaxing day out with the kids, or somewhere in between, Classic Harbor has a trip for you.

Classic Harbor Line Key West

Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green Flash." Experience the magic and romance of sailing at dusk as you sip champagne and watch for dolphins and other marine wildlife in the surf. Your friendly captain and crew will teach you the basics of sailing and even let you take the wheel. So, take a turn at the helm of one of the fastest schooners in the United States, book today!

Key West Sunset Sail on America 2.0

Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green...

There's no better way to experience the gorgeous sunsets of Key West... it's how we celebrated our 20th wedding anniversary. The America 2.0 was beautiful and the captain and staff were impressive. We absolutely loved it!

Amazing experience!

The staff was outstanding.  They took excellent care of us all night.  The ship was just the right size for this adventure.

Sunset cruise to remember

The crew was extremely knowledgeable, very professional, personable great fun!!

Amazing Experience

Explore the high seas in style on the Schooner America 2.0, the namesake of the first sailboat to win America's Cup in 1851. This stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating for the whole family. The sights you’ll see along the way include a waterside view of Fort Zachary Taylor, the famed Sand Key Lighthouse, Mallory Square, and Sunset Pier. So sit back and feel the warm breeze dance across your skin as you watch the sights of the beautiful water around Key West. Book your spot today!

Day Sail Aboard Schooner America 2.0

Explore the high seas in style on the Schooner America 2.0, the namesake of the first sailboat to win America's Cup in...

The crew was wonderful and the boat fantastic!

Excellent

Excellent Captain and Crew.  Superb sailing with good winds and beautiful weather

Sailing

We absolutely loved the boat and crew. It was perfect weather and we got to have a blast when the sails went up. They only thing is be you have to pay for beer and wine. They are NOT complimentary like stated on your Day Sail ticket. They also do not provide snacks as stated as well. This is only for the sunset sails.

Classic Harbor Line Key West Activities

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