All Locations

We at Classic Harbor Line offer ticketed cruises like sightseeing boat tours, sailing trips and private yacht charters . Our locations are in Boston, NYC, Newport and Key West. We aim to create an elegant atmosphere to give you a boat ride that will stay close to your heart for years to come.  You may pick from a variety of creative activities including events like Beer Tasting, Wine Tasting, Brunch, Sunset Sailing, City Lights Cruises, Harbor Cruises and more. 

Our ticketed cruises and boat rides are available for locals and visitors alike in any one of our four locations.  The boats are also available for a private yacht charter.  So, step aboard and let our professional crew cater to you. You will sail with us like royalty. 

Classic Harbor Line Boston location at Rowes Wharf behind the Boston Harbor Hotel


Our Boston vessel schooner Adirondack III and motorboat Northern Lights are located in the heart of Boston at Rowes Wharf just behind the Boston Harbor Hotel. Enjoy a day sail aboard our 80-foot sailing vessel or enjoy a Boston Harbor Island Cruise aboard the elegant Northern Lights. Let our crew treat you with professional hospitality and enjoy the day on the water.

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Classic Harbor Line Newport RI Ticket Booth Check in


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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Classic Harbor Line Key West Crew on the Schooner America 2.0

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 the only dinner cruise aboard our classic 1920's style yacht Manhattan for an evening of elegance and style. Located directly behind the famous Schooner Wharf Bar, you are sure to have a memorable Key West experience.

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Classic Harbor Line New York Location with Schooners Adirondack and America 2.0 and Yacht Manhattan and Kingston

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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