Flying into San Jose airport puts you and hour and a half to two hours south(and opposite from SF) to Monterey/Carmel and an hour north to San Francisco. I live in the Peninsula/San Jose area and while it's an interesting area with literally hundreds of hotels and motels/all brands, I wouldn't stay there with Monterey and the City beckoning. If you don't have time to make the swing south and then north again, you might consider staying in Half Moon Bay on the coast for your first night or two and then on to San Francisco with the wine country beyond. It's charming little seaside town catering to tourists with some nice restaurants and a couple B&Bs and one expensive but dramatic Ritz Hotel. You travel north towards San Francisco from the airport for about 40 minutes and then go west at the 92 highway towards the HMB about a 30 minute side trip. If you have limited time and still want to do both major areas, don't make the mistake of taking the coast route from Monterey back to San Francisco. It can add another 2 to 3 hours to the drive and the route is blocked near SF because of a landslide. Interesting though, if you do want to drive the coast route anyway, you have to detour thorough Half Moon Bay back to the main highway.

Peter in Foster City, California