Advice: Are my friends (and me) insane?

The Rockies would come as a blessed relief after the thousands of miles of flat, windswept plains you'll cross between Toronto and Calgary. It won't be very interesting as rides go. Why not fly to Rome or Athens or somewhere like that and ride back to the UK?

+1

The prairies will be a combination of boring as shit, flat as a pancake, and windy as fuck. And this will go on for hundreds and hundreds of miles. Could quite easily end in tears.

I think Toronto to Vancouver is the wrong way to go. If I were going, I would do this: land in St Johns, Newfoundland and head south; take the ferry to Nova Scotia, cycle to Halifax (haven't been, but supposed to be a really cool city), then west; catch a ferry to Prince Edward Island and cycle across it; take a ferry to New Brunswick and start heading west; head along the fleuve St Laurent) through Quebec and onto Montreal (must go to Montreal!); from Montreal you can hit up Ottawa (or skip it) and then Toronto. Could even head to Algonquin Park after Ottawa before heading to Toronto.

This is the ride Sheldon would tell you to do (because it goes through Quebec)

Check this out for some (lots of!) journals though: http://xcanada.roosmachine.com/yearbody.html