South maybe not so good, down CA 1 to Half Moon Bay SP >Santa Cruz (New Brighton SP) > Watsonville Area (Sunset Beach SP) and then? That's the tough part (my opinion) - either backtrack or take public trans back to SF.
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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.