Well, I'll give my two cents assuming that you are trying to drive on fun roads. I would take I-10 to Banning (just past Palm Springs), head south to Idyllwild, 243, to 74, to 371, to 79. Then if you really want a crazy road, head up to Mt. Palomar. Otherwise head south to Julian, and all the way down to 8. If you want to stay in down town San Diego, the best garage I have found is right next to the baseball stadium. Avoids valet's and within walking distance of most downtown hotels.
Now PCH is just a 4 lane red light and traffic road all the way until Morro Bay. About half the time you'll have a view of the water. You can probably make Santa Barbara in the first day. I would seriously consider making a detour to Ojai and take 33 north. You can either continue back to pch that way, or you can turn around and do it again to get back to the coast. Skip this road if there has been recent snow.
The next time I'm in the Big Sur area I plan on staying at the Ragged Point Inn. (
http://raggedpointinn.com/ragged_point_gallery_details.php?id=7) Great view, food and bar. I'm sure the Post Oak Ranch is great and all, but I'll take a thousand less a night. The secret to Big Sur, if there is one, is to go in winter when it's not raining, and if you really want a traffic free experience, get up early and hit the road before every one else. Drive north for about an hour, then turn around and do it again. This is the best section of the entire coast and great fun when the road is open.
In San Francisco I like the cliff house (
http://www.cliffhouse.com/home/index.html) I know it's a tourist trap, but the view is amazing. Ships, dolphins, crashing surf. On leaving town, you have three options. If the weather is forecast to be good for a few days, you can head to Lake Tahoe. There are at least three passes you won't make it over if it is snowing though. But if it's clear Lake Tahoe is awesome with white mountains and the sun shining. Head over to 395 and south past Mammoth, then you can cut through death valley (through Vegas and Kingman), or just take 395 all the way to Barstow and then 40 east or continue south to 10 east. Or you can take 5 south for the same options. (I would head to San Jose and take 130 over the hills), or you can head back along the coast all the way back through LA, or at San Louis Obispo you can take 58 east to Barstow.