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Drive down CA Coast

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So I am trying to plan a trip down the CA coast; I am flying into Medford Rogue Valley Airport on 9/19 and out of Ontario Airport on 9/30. I would (ideally) like to go to Crater Lake on 9/20 before coming down to CA. I want to drive down the coast, only making a detour inland to go to Oakland to see a cousin and friend. Otherwise, down the coast. I'd like to drive the whole thing (down to San Diego) and then come back up to Corona and stay with family from 9/26-9/30. The major sites I would like to see are Crater Lake, the Redwoods (which forests/parks are the best? I saw a lot of them on the map!), Point Reyes Seashore, Muir Woods, Hearst Castle, Pebble Beach golf course, Carmel/Monterey??, Santa Monica pier...I think I could drive to Sequoia NP from my uncle's...First of all, is this doable? If so, does anyone have a suggested itinerary? Also, are there any additional recommended sites? If there isn't enough time to go down to San Diego, I could always just cut over from LA to Corona.

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