RE: Monterey California
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PCH is a beautiful drive, I recommend it. My wife and I did most of it on two separate occasions. Depending on what type of scenery you like, I recommend starting near San Francisco and drive south to Santa Monica. This was our favorite section and you can drive it in a day or stop and get a hotel part way.
We've also done SF north to Oregon, it is also beautiful but the road is more windy and it took us around 12 hours to drive. My wife started getting car sick on this section.
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Oh wow, that sounds pretty intense on the northern section.