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I've done most of it with the exception of the Olympic Peninsula, which I hear is beautiful. In fact, I used to live by 101 in California for a couple of years, south of San Franscisco; that part of the road is okay, but you really want to get on Rt 1 which hugs the coast through Monterey and Carmel. Above San Fran the same is true.
North to south, south to north makes little difference. It will look different which ever way you go. I haven't done it 40 in years, so like most things, it's probably not quite as nice as I remember it. However, the Northwest coast is so unfriendly (cold water, chilly weather all summer long) that it remains relatively empty.
The best time would probably be in October, when in the Northwest the land and sea temperatures stop fighting each other for a brief spell, when California is not too hot, and when all the tourists who have children have gone home. And avoid driving, if you can, on weekends, unless you like being in a line of cars.
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Gregory
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