Wow! What an insanely busy itinerary.

IMHO you would be better off to skip Napa, do San Francisco on your first full day and leave for Monterey a day earlier. That would allow you to add a day to the trip south on the Coast Highway, stopping for the night near Big Sur, San Simeon or Cambria. If you want to do a wine tasting tour, do it in San Luis Obispo County or even Santa Barbara County along the way. In that way, you might actually have time to see some of the sites you mention rather than just driving by at 60 mph.