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Would you drive the Ca. coast starting from...

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Would you fly into Portland, Or. and drive down the coast leaving from San Diego? Or would you fly into SD and leave out of Portland? I just don't want to start with the warm sunny weather and end up in the cooler misty rain. Is that the way it is in Or. at the end of June? Many people have talked about the drive south being worse on the driver and I want my husband to enjoy it too. Thanks for you help.

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