Key West, FL

All Locations

Classic Harbor Line Boat Tours are located in NYC NY, Boston MA, Key West FL, and Newport RI.  Ticketed cruises are available for purchase as well as renting out one of the boats for a private boat charter.  Classic Harbor Line offers a variety of boat cruises that is unique to its location. The Key West location offers a premium sailing experience aboard the Schooner America 2.0 and specializes in a classic Key West Sunset Sail, and Afternoon Day Sailing.   Schooner America 2.0 holds first place for over 6 years now for every single Wreckers Race in Key West.  Come sail with us…… 

Key West

This vacation island is the perfect getaway. Jump aboard the legendary schooner America 2.0 for a sail in the emerald green waters to make your trip an exceptional memory. Or enjoy an afternoon sailing with the dolphins. Located directly behind the famous Schooner Wharf Bar, you are sure to have a memorable Key West experience.

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ur Boston vessels Schooner Adirondack III and Yacht Northern Lights are located in the heart of Boston just behind the Boston Harbor Hotel. Enjoy a day sail aboard our 80 foot sailing vessel or enjoy a Bridge and Locks cruise aboard the intimate Yacht Beacon. Let our crew treat you with professional hospitality and enjoy the day on the water.

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Newport is known for sailing and that's exactly what you can do on the 80-foot schooner Adirondack II. Enjoy a day of sightseeing the cliff walk and take in the mansions. Then sail away for a sunset sail in luxury and comfort on Adirondack II, located at Bowen's Wharf. You are sure to enjoy this old and classy sailor town.

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New York

New York City is our largest location and operates five vessels. New York City’s excursions are perfect for locals and visitors alike. Take to the water and fall in love all over again as you see the most famous skyline in the world from the perspective of a classic vessel. Enjoy a sail or take an educational architecture tour; you are sure to be impressed and come back for more. Located at Chelsea Piers.

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Although we do not run public trips out of Shipyard Marina in Hoboken, we do offer private charter pick up for those that would like to celebrate a Birthday or take a company out for a corporate event without having to come to New York City.

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