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Boston Sailing Cruises

Relaxing sunset cruises & sailing tours.

Gorgeous Views and Fascinating History

Soak up the gorgeous views and fascinating history of Boston Harbor on a sailing cruise. One of the most popular Massachusetts pastimes, sailing gives you a whole new appreciation for the city and the natural landscapes that surround it.

You won’t soon forget the peaceful ambiance of a sunset cruise aboard a classically styled schooner. Whether you’re trying to plan a romantic night on the water or want to see Boston in an entirely different way, you can’t go wrong with a sailing cruise.


Sail the Seaport District & Beyond

There’s so much to see around the historic Boston Harbor. Starting in the Boston Seaport District, your sailing cruise treats you to a great view of the city skyline, with many newly constructed buildings and architectural gems that you might recognize. The moment you leave the dock, you’re sure to enjoy the incredible scenery of the harbor. Keep your eyes peeled for Harpoon Brewery and Fan Pier. There are several Inner Harbor Islands that your captain will point out, like Castle Island, Long Island, and Spectacle Island. See landmarks like Fort Independence and Long Island Head Lighthouse.

For a more special experience, book a sunset cruise and share a memorable evening with friends or family. Seeing the sunset over the harbor is a magical experience, especially from a beautiful, classic schooner. No matter what time of day you choose for your Boston sailing tour, you’ll feel right at home with capable captains aboard a sleek, smooth vessel.

Experience Boston Harbor on a sailing cruise! Book online today.

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