[carom]

My wife and I did a similar trip from Calgary down to San Francisco a few years ago. Our trip went:

Calgary-Vancouver-Portland-Eugene-Coos Bay-Eurika-Napa-San Fran-Pacifica-San Jose-Klamath Falls-Fairmont Hot Springs-Calgary

Some highlights were:
Beer and breweries! Everywhere we stopped we went to a brewery or brewpub.
The trip was originally planned around going to a University of Oregon football game and watching the Flames play San Jose. I also wanted to spend as much time off the interstates and on the coast as possible on the way down.
Portland was very cool, voodoo doughnuts are great. Great place to explore on bicycles and some of my favourite breweries.
Coos Bay has some really cool sand dunes on the coast and we rented a side-by-side (wife didn't want her own quad) and ripped around the dunes for a few hours. Mid week in November we had the dunes all to ourselves.
Quite possible my favourite day of driving of all time was from Eurika to Napa because we did the Avenue of The Giants then California State Route 1 where we jumped over the mountains at Leggett and along the coast all the way down. Definatley much slower than the interstate, but fun driving and amazing scenery. North coast brewery in fort Bragg was a nice lunch stop.
San Fran was cool and we did a couple days surfing in Pacifica before going to the hockey game.
It was a couple big days back to Canada from San Jose with the first night stop in Klamath Falls. Crater lake the next morning (the road up was open, the road around the crater was not), a stop in Bend for lunch and powering across the boarder around 3 am. I just couldn't stand the thought of another night in a Hotel. I wish we had been able to spend a day or two in Bend, seemed like a really cool place.

This trip was the first 2.5 weeks in November 2010. We didn't have chains and didn't have a problem. Just pm me if you have any specific questions.