Welcome to Classic Harbor Line - Boston

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Classic Harbor Line: Boston

At Classic Harbor Line, we are dedicated to providing the most impeccably luxurious and hospitable sailing experience in Boston.  Our guests can look forward to the privilege of being escorted on a breathtaking excursion aboard the most elegant sailing vessel in Boston Harbor, the schooner Adirondack III. If you’re a first time visitor or a seasoned local, sailing on the Adirondack III will provide you with a new perspective on the city of Boston. While aboard our stylish schooner, you will be treated to views of the spectacular Boston skyline, historical sites, harbor islands, and perhaps a glimpse of some of our elusive wildlife, such as: the harbor seal. So, come on out and experience the best sightseeing adventure in Boston! And please, kick up your feet because we’ll do all the heavy lifting (and drink pouring)! 

Whether experiencing one of our many public events or privately chartering the schooner you will be amazed by the comfort and beauty of the Adirondack III and her crew. Tickets may be purchased for a Classic Day Sail, Sunset Sail, City Lights Sails, Boston Harbor Picnic Sail, or our Sails & Ales featuring Harpoon Brewery.

If you’re looking for a new and exciting experience to host your next company outing, consider the schooner Adirondack III for group sizes of 40 or less. Adirondack III has hosted many memorable corporate events in addition to weddings, anniversaries, marriage proposals, team builders, and birthdays. To get more information on privately chartering the schooner Adirondack III for your next event, go to our Private Charters page.

Classic Harbor Line is known for operating some of the most stunning sailing boats and classic yachts in New York, NY; Newport, RI; Key West, FL; and Boston, MA. In addition to our beautiful vessel, we are also renowned for our excellence in hospitality and customer service. 

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