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On the other hand...
Maybe consider taking the Sierra Cascades route to Sisters and then the TA to Florence and follow the coast south from there. Three weeks is probably a bit tight on the time for that though. Check the mileage and decide if that can work for you.
This is the rainy season. Fronts come down from the Gulf of Alaska so they are cold and wet. Generally the wind is from the north but during this time they could come from the south when a low pressure zone brings in the cold and rain. This definitely not the tourist season so road traffic will generally be only locals. It is also possible that parts of the route nearer to SF could be closed due to slides. When you get to Cambria check with CalTrans to see if HWY 1 is closed anywhere along the route. http://www.dot.ca.gov/
I just checked the web site and there is a slide about three miles south of Gorda. The road is still open but be prepared for delays and construction equipment in the area.
Thanks for all the useful advice. Very handy. If anyone else could help on a couple of queries. How many hours cycling in daylight can we expect in late November/December in the area? Are there enough motels open on the Pacific Coast at that time of year?
snip> My first thought was the coastal route, but if I want to see the first stage (Nevada City to Sacarmento) it looks like a better (i.e. direct) route is to Klamath, Altamont and down.
I know nothing, I've only been to OR once and that was for business in Portland 20 years ago. I've only just started looking at this and have gotten no further than trying to pull info off the 'net, which hasn't been a fruitful search. About all I know is what I can surmise from Google Maps.