Hi Daryl,
Call the Culinary Institute in Healdsburg, terrific food/wine and very nice rooms.
http://www.ciachef.edu/california/
From Gilroy there would be several really nice roads. Possibly out to Amador County also.
http://www.viamagazine.com/top_stori...s/amador05.asp
Follow the links for info-----
TR
TR