Since you're stopping in Monterey, check out Big Sur. It's south of Monterey.
Sunset and cocktails at Nepenthe's.
Maybe Pfieffer Ridge.
17mile drive, lot's of money lives there.
Pebble Beach golf links, cocktails at the Tap Room.
The Inn at Spanish Bay, sunset and cocktails on the patio at Roy's.
The Aquarium.
May as well go down to Cannery Row.
Laguna Seca.
Aptos, cocktails and dinner at the Cafe Rio.
Santa Cruz, resort town, eat and drink.
Hiway 1 up the coast to Pacifica (just south of SF).
You should at least drive through SF. Since you're there. Lombard Street and whatnot. Lots 'o good eatin'n drinkin'.
Oakland, for a good mugging. (j/k)
Oh yeah, Napa might be nice. Wine tasting.
Infineon Raceway? (Sears Point)