I don't post here much, but I'm a native of seacoast NH/ME and I work in Portsmouth. If you have any specific questions let me know. Bangor specifically is a little further north than I'm familiar with but DH is a native of ME and got around the state more than I. This website is pretty informative for things to do in Bangor: www.visitbangormaine.com/index.php?id=339&sub_id=282
I'm afraid I don't "get" Boston as a destination :^). Reading that tour list, it seems like (and I'm truly not trying to be unkind) countless other cities in America: a couple museums, a park or two, some local history, a pretty neighborhood or two, some nice restaurants. On paper, it could be anywhere. What is it that makes Boston Boston? We've done Philadelphia before and all the Revolutionary sites there - someone who's been to both will have to tell me how similar they are. Vacation days and dollars are limited for everyone, and we try to choose destinations (other than when we're just chilling on a beach for the sake of chilling on a beach ) with "Is there something at this destination that I can't experience elsewhere?" in mind. That's what I'm not understanding about Boston.
heygrey, we didn't like Victoria because it was an in-between: neither a glittering, 24/7 city like London or New Orleans, nor a relaxing escape. It was pretty, yet average - with city parks and a couple museums and a little history and some nice restaurants. Culturally, it seemed just sort of generically North American, like you could move it anywhere on the continent and it would fit in. I don't mean to insult it - we had a fine time and it's a fine place, but that's it - it's just fine, not wow, not "I had a great time," not "I can't wait to go back." And it was holy expensive, batman! (By comparison, even Maine's August prices have surprised me as very affordable.) Spending what we spent on "fine" made us more than a little cranky.
I feel like Maine checks the bucolic escape box and its culture of lobster and lighthouses and fishermen and quintessential "summering" is something I know we haven't experienced before. Though my main concern is still whether or not there's enough there that's unique enough and special enough to "earn" my vacation days and dollars.
As a previous poster mentioned, the point of visting Boston is to see/experience the sites of the revolutionary war and to visit and be immersed in a city full of universities and academics. You can experience the Boston accent - it's unique
Beyond visiting Harvard, MIT, and the Freedom Trail, this is my take on the things that make Boston interesting.
Boston is has a more European feel to it than most US cities. It is extremely walkable, not based on a grid, dense, lots of mixed-use buildings, has decent public transit. Most of the buildings and architecture pre-date the 1900s. Though most structures are old; there is not much notable architecture here, with a few exceptions. Frederick Law Olmsted designed an integrated network of parks here called the Emerald Necklace. If you're really into landscape design or Olmsted, it's worth a visit. Walter Gropius, the founder of the Bauhaus movement, worked as a professor at Harvard and had an interesting home in Lincoln, MA.
If you're into American Literature, you can see Louisa Mae Alcott's house in Concord, Walden Pond outside of Lexington, Ralph Waldo Emerson's house in Lexington, and Nathaniel Hawthorne's house in Salem.
If you like art, my two favorites in the Boston area are the Isabella Stuart Gardner Museum and the Decordova Sculpture Museum in Lincoln.
If you like music, you can see great live shows every night of the week. The Middle East, Toad, The Cantab, and Abbey Lounge are some of my favorite places to go.
To be honest, I don't love living in Boston, but I always recommend it to people as a good place to visit.