East Coast or Iceland?

So i've been working on my epic trip I'm going to be taking when I get out of school...I finally decided on a few things.
       1.  Doing the whole world in one go is impractical and more than likely would end poorly
       2.  Doing a continent at a time may be more successful
       3.  I'm calling canada, ice land and greenland a continent...and they will be my first spots
I just don't know where or why or when from there.  Canada has its own rail and air systems and the US has its and they dont always interbreed very well...so I might just walk to iceland...there is only one flight that I can see that goes their and it leaves from a couple places in canada and the US...boston being the one that I'm considering.

It all sounds so very fun.  As long as I get to churchill, MB, and see the Aurora Borealis I'm happy!