I cycled solo from Vancouver up to Fairbanks in the summer of 2008, awesome trip. Wind was really not a big factor. I rode up Vancouver Island to Port Hardy then took the ferry up to Prince Rupert and then on to Skagway. Going up White Pass to the Yukon takes you from sea level to 3,292 feet in 14 miles, but the views are spectacular:
I saw a few cyclists going the other way but none going my way, especially going up the Klondike and the rugged Top-of-the-World Highway. There are stretches of unpaved road, but if you go up that way, you'll ride high along the ridge of mountains to get to the northernmost point of entry by land back into the USA:
A water filter really came in handy as there were few services along the way so brought at least a couple days worth of dried food and took my water from rivers and streams. The river banks are steep and slippery, and the water often runs fast and silty so a cloth bucket came in handy to fetch water:
I remember when I got to Tok, AK it felt like such luxurious civilization. I enjoyed the Yukon the most, awesome landscapes and interesting people. I could have cycled down to Anchorage from Fairbanks, but as a treat I took the Alaska Railroad which is one of the must-ride scenic trains in the world.