Places for good info on US-Canada flights?

Hi all,

Thinking about taking the 172 from Boston to Montreal because it just isn't
cold enough here in New England. I love Montreal but the 6+ hour drive is
just a little too much for a weekend trip and it looks like the Skyhawk
could meet the airlines on price for 2 people and probably beat them on time
if I figure it door-to-door. With airways routing it looks like about
200-220NM. Can you really do it in two hours, wheels up?

I've looked at AOPA and googled around but nothing provides a nice, concise,
"Here's how it's done" guide. What documents do I need? Are 3" N-Numbers OK?
How do I file the flight plan (I'm assuming it's simpler to just go IFR)? Do
I need a radio license? Am I better off flying straight to my destination or
should I land and clear customs near the border?

Ideally I'd love to hear a narrative of this trip done within the past
couple years by somebody else, but I'll take whatever I can get.

TIA,
-cwk.