Classic Sail Boston has been showing people the best of Boston Harbor since 2014. Our goal is to make each of our charters a memorable and unique experience for our guests. Whether special occasion or just enjoying an afternoon on the water, we do all we can to create the sail you're looking for. Sail with us around the inner harbor to see the BEST of Boston including Seaport, Southie, Castle Island, Spectacle Island, Eastie, Charlestown, and The North End. Let us regale you with the history of these places, or just listen to some music and enjoy a leisurely sail around the harbor. We specialize in hosting private events; birthdays, anniversaries, proposals… we do it all. Complimentary soda and water are always on board and you’re welcome to BYOB anything else you wish! Convenient pick up location in Boston’s Seaport District, with custom pick up/drop off locations throughout Boston Harbor upon request.
