The trip!
Here's my report back guys - I owe you at least that for the nice suggestions you gave me.
First off, on the way from Montreal, we stopped at the New Hampshire liquor store (a classic!) We then headed to our hotel in Medford. Cheaper hotels, great transportation to the City. So on Saturday we walked the Freedom Trail and saw some nice spots. We were too late at the Naval Base to visit the USS Constitution and the other WWII battleship, but we saw the canon being fired, which was a nice experience.
During the walk, we DID stop at Mike's Pastry for a canolli. It was me and my gf's first cannolli WORTH THE WAIT! Thanks, a5liz!
We also we lucky to book a reservation at Terra Mia. My gf's meal was out of this world, but mine was just ok. Still a good experience. Cafe at Vittoria afterwards as well! Thanks, A5orBust!
Our walk in Charlestown was beautiful and perhaps the nicest area we've seen. That was a very charming neighborhood! We also liked North End, Faneuil Hall, Boston Commons and all the other sightseeing spots along the Trail.
On Sunday, we did the aquarium, walked the financial district, crossed to the southern part (where we did stop at Barking Crabs for some seafood - NICE! Thanks attam! Then, we drove around to Newbury and the Prudential tower before heading off to walk around Harvard.
Great weekend! Two conclusions came out of our weekend.
1- 2 days AIN'T enough to enjoy Boston, we'll come back next year.
2- It's actually one of the few US Cities where I would definitely live. It is super nice!
Thanks to all of you for your nice suggestions. Our next trip will be to Washington, D.C.!