Key West, FL
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Key West: Sailing Adventure America 2.0

Classic Harbor Line Lots of birds flying out to the ocean with the Schooner America 2.0 bow in the picture

See what dedication to providing the most perfect hospitality and sailing experience in Key West looks like. It is a breathtaking excursion aboard the most elegant vessels in the local Key West fleet: Schooner America 2.0.

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Shipboard Soirees

Simone Boyce - Fox 5 NY Schooner America 2.0 sailing with crew and guests on deck as the golden sun peaks through the sails for a Key West Sunset Sailing experience

For an elegant off-site location, charter a classic 1920s yacht in Boston; Newport, R.I.; New York, and other East Coast ports. Classic Harbor Line’s fleet of vintage vessels are perfect for team building and corporate outings; onboard wine tastings and history lectures can be arranged. Cost: $775 to $1,600 an hour, depending on size and […]

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This cruise is really about sailing

Classic Harbor Line Crew raising sail on the schooner America 2.0 for a afternoon of Key West Sailing

There is a perfect moment of sailing on every voyage. It happens just after the engine is shut off, after the sails snap at the wind on their way up the mast, after the boat falls off the wind’s nose searching for her heading. It’s when she surges forward under her own power, slicing through […]

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