Nice pictures!
That Clippership Wharf is in the Jeffries Point neighborhood,
which I covered before. I suspect there were no tourists, and very few people, because it was winter. But I was in Jeffries Point for the start of summer, and there were only a few people in Piers Park taking in the skyline views at night, and then only a few neighborhood people jogging when I went the next morning as well. It's a nice neighborhood with great views and seems to be just for locals. I suspect that the tourists get their skyline shots from Charlestown, when they go to or near the USS Constitution.
My uncle is a lobsterman and regularly brings his catch to central Boston for wholesaling and retailing. There is a good chance you ate one of his lobsters if you ate at Quincy Marketplace.
Have you ever ventured well outside Boston when you visited (although I'm guessing you've been there just a few times since you mentioned it's been about 20 years)? Say, to Plymouth, Cape Cod, Salem, or Gloucester?