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Drive from Portland to San Diego

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I'm considering doing this trip from Portland to San Diego, starting on 23rd or 24th of September.

--> How long do you think I need at least to drive all the way down to San Diego, stopping to take some photos on scenery views. (I'm a French photographer)
--> is the coast road crowded at that season ?
--> what are the "must see" things on the way dow to San Diego ?

No stop to San Francisco since I'll be visiting the city before, as well for Seattle and Portland, that I'm planning to leave on the23rd or 24th as start of my road trip.

I'd like to be in San Diego on 29th/30th September the latest
--> do you think it's good enough to make it and enjoying the view on this trip ?

Thanks for any help you could provide :)

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