Yeah, that's the thing, I'm not sure if we want a relaxing trip or a doing something trip. If I did do BC it would be Squamish (dunno if I put on the list).
And yes, Highbury is a must if we go to London. Vienna is over priced right now due to Euro 2008. And I agree on the Italy part, but I've never been to Rome and it could be a good landing point and go explore the country from there.