Re: Montreal vs Boston
In Boston you can go to Quincy market and the pier. There is also Kennedy memorial/residence. Cambridge is interesting if you goto Harvard Square and check out the university.
There is a lot more in Montreal. Old Montreal, Old port area, Mount Royal, St. Catherine Street, Biodome, Biosphere. You can also goto Quebec City which is 2 hr drive, worth to watch Old Quebec (400 year old city inside fort). You will fall in love with Quebec and Montreal. Boston downtown scene is boring.