re: Napa/Sonoma/San Jose/Monterrey Help (Wineries too)

I'd pick different areas and concentrate on one a day. Getting off the valley floor will also (more times than not) get you much more authentic/less tourist driven experiences. Here are some of my favorites in Napa:

Pritchard Hill
Chappellet
David Arthur
Ovid or Continuum for an over the top high end experience

Conn Valley
I really love both Forman and Seavey. Anderson Conn Valley is right there as well, and I liked it too...just not as much as the other two.

Howell Mountain
Dunn, Outpost, O'Shaughnessy all are great wines for a (relatively) not absurd price. I've also heard good things about Arkenstone, but I haven't been there personally.

Spring Mountain
Behrens Family is always a great tasting. Pride is a must do (at least once) if you're in the area. Vineyard 7&8 is supposed to be really nice as well.

Valley Floor/Silverado Trail
I lumped these together, but they can be pretty far apart. Shafer is a nice tasting - good wine/people. Spottswoode is another favorite. Hall Rutherford has a very nice tour too. Schramsberg has a great and unique tour as well. I know a lot of people like Larkmead, but I haven't been there.

I don't have as quite much experience with Sonoma (which is a pretty wide area in general), but some of my favorites from there to drink/visit:

Ridge
Paul Hobbs
Bedrock
Carlisle
Ramey

Frank Family is great choice. Also, if you have the time (and don't mind spending the $$$ for the tour, Castello di Amorosa in Calistoga has great wine and is just beautiful.

Being a Sonoma County resident since '85 may I suggest Cafe Citti on Highway 12 for some rustic Italian food (best gnocchi I've had outside of my Zia's house in Lucca) and it's not too pricey.

Also, if you get to the south end of Sonoma County, two small, but extremely good restaurants in Petaluma.....Le Bistro, on Petaluma Blvd. South between E and F Streets (very small, great food) and the Wild Goat Bistro in the Old Mill, Petaluma Blvd and B streets.(Also very small, but great food...FYI, it's been extremely cold out here in Sonoma County (especially the Southwest part of the county. We hit 19 degrees last night and will be in the 20's-30 at night for the next couple of weeks...Need rain, 2 year drought)

One last place, if you're looking for a quirky place to have a drink, Volpi's on East Washington at Keller...Skip the restaurant, food way over priced and not very good, go to the back room which is a 15x20 room bar that is a left over speakeasy from prohibition. Can get a drink next to a hipster wearing skinny jeans on one side and a dairy rancher wearing his slickers and rubber boots on the other....

Have a great time....

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thinking Carmel, Big Sur, Monterrey, Palo Alto, Berkleley, Oakland, etc.

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, oh forgot to ask, you do realize that Big Sur, Carmel, Monterey is definitely a 1-2 day trip by itself and Berkeley-Oakland then onto Palo Alto is a day all unto itself...Do to distances and traffic patterns...

Also, if you are going from Berkely-Oakland to Palo Alto, avoid the desire to take what either a map or GPS route that will send you over the Dumbarton Bridge...It dumps you out in East Palo Alto (San Mateo County, Palo Alto=Santa Clara County-Stanford) which rivals or surpasses the worst parts of Oakland or New Orleans.

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Frank Family is great choice

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This was a great tasting. We actually met Mr. Frank, who started his business from proceeds of producing the movie "pretty woman". Nice Guy.

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Castello di Amorosa in Calistoga has great wine and is just beautiful.

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No flame intended, but I actually did not enjoy this. The tour of the castle is cool I guess if you are into that kind of thing, but the wine IMO was a step below most of the other wineries listed in this thread. JMO