For your Canadian part, VIA rail is one option that could allow you to hit Toronto, Montreal, and Quebec city if you'd prefer not to drive as the train is downtown to downtown, so you avoid the hassle and time of getting to/from the airport and the cost isn't ridiculous. Driving could be another option if you want to see sights outside the cities but don't try it in the winter if you aren't used to winter driving. NYC-Washington is also trainable.

Otherwise, I'd likely think flying is the easiest way to get around as long distance trains are not fast at all and the distances are much greater than in Europe. But the LAS to SFO route could be by car as you can tour around in the wine region.