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Trip to Cal to drive the coast starting in San Francisco in Sept for 9 days

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My husband and I just booked our flight into the Oakland airport for next September. He has never been to San Francisco and really wants to drive the coastline south in a convertible. We fly in on Saturday, Sept. 27th and fly out of the same airport on Tuesday, Oct. 7th. Now the fun begins as we decide on our itinerary and figure out how to see everything we want to see without feeling too rushed. We're not sure if we should drive the coast down to San Diego and then plan on dropping the rental car there and get a one-way flight back to Oakland or if we should just plan to drive not so far down the coast and then drive it back up at the end of our trip. We have both been to San Diego, so it is not necessary that we go all the way down there. Does anyone have any suggestions on how to best utilize our 9 full days between San Francisco and driving down the coast? Any suggestions would be greatly appreciated. We are just starting our planning process so we don't have any accommodations or anything else booked besides the flight.

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