Or are you thinking you would like to head north, say inland first (like maybe the Napa Valley), head out to the coast, and then back to SF?
How familiar are you with the area?
I'll offer what I can based on your reply.
Santa Rosa, CA
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. . . You still need to cut in (East) to the official route to cross the Columbia unless you brave the Astoria Bridge which is scary when cars / trucks lose patience with you.