This is a sailboat ornament that my wife gave me in memory of our days sailing in Boston Harbor. We had to stop when her arthritis made it difficult for her to hold the sheet.
The sailboats were kept at Pier 4 in Charlestown (Pier 1 is USS Constitution.) You needed permission to go down to the dock where the boats were tied up and you had to check out the sails, they weren't kept on the boats. (And a sailboat without sails is pretty useless.) The sails had numbers on them; they could tell from a distance if anybody was misbehaving.
Also, Boston Harbor is regulated by the Coast Guard - not the state.
There was no license needed, but you had to pass a learn-to-sail course that included basic boat handling for a sailboat, Coast Guard requirements, and right-0f-way rules (which boiled down to "They're bigger than you stay out of their way!") It also included man-overboard drills and rescuing someone in the water - which is bit tricky in a sailboat without an engine.
There were three levels of qualification: the lowest meant you had to stay close to the dock and and only sail in light winds. The second level allowed you all over the inner harbor and in stronger winds. The third level had no restrictions.
Were you required to have a captain license to operate your sail boat in the harbor waters? I had a little Snark sail boat back in the 70s and other than a Kansas state registration no license was required for operating on state lakes. Paul