O Canada

A bit more research on the Toronto thing. The Goldleaf Rocky Mountaineer trip costs a bit over $1300, but apparently the seats under the "dome" canopy are the best way to do the trip and that's not because the on-board tucker makes up for the price difference. There's also a three-day service Vancouver-Toronto in the classic 1955 railroad cars. The "Romance by Rail" package sounds really nice, for about the same price. That'd eliminate mucking about with another air trip.

I can sell Kerri on either of those, I reckon!

Now, to either win that travel prize or come up with the money another way...