Jim from Boston, can you elaborate on some of the spots you've hit on your tours? I'm always looking for new things to to do. I first moved to Brookline 10yrs ago, gf lived in Allston so hung out there a lot, then we moved to Davis Sq in Somerville for most of that chunk. Now we're a few towns north in the Melrose Highlands area. Funny about the concept of it being hard to cross the river. Boston people stay on the Boston side and Cambridge/Somerville people stay on that side. For that reason i know Cambridge/Somerville best. We also both work in Cambridge.
+1 on a tour! I've been on four duck boat tours with various visitors and love them! I always ask to drive, but they always give it to some punk 8yr old kid! ha ha ha. I've never done a trolley tour but that'd be good too. The point is to get a lay of the land and learn some interesting history and facts. Example, at Bean Town Pub you can drink a Sam Adams while looking at Sam Adam's grave!
We very rarely venture down to the shopping/china town district. Pretty much only to Jacob Wirths for a piano night or for theater stuff. And "hot tea" in my younger days
I'm sure there's lots to see and do. Seaport area is blowing up. Seems like we're brought down there for various events lately.
We got married in the Boston Public Garden and had our rehearsal dinner at Stoddards which is one of our favorite spots. It's hard to recommend places with teenagers as our spots tend to be food and alcohol centric.
Lots of breweries in the area.
I've lived all over the US and kind of moved to Boston on a whim. Glad i did, it's a great little city.
If the kids are old enough, could you split up for a few hours? That might be exciting for them. It's very easy and safe city. But yeh, it's big enough to have a lot of stuff to do, you'll need to be more specific about interest. food, music, art, history, academic'y stuff like Harvard/MIT/BU campuses.