Since no one else has, I'd say that going south you want to take 35/Skyline until about Highway 92, then Canada Road until Woodside, then up Woodside to Skyline again, and take that all the way south over 17. From there it gets a little tricky, you want to get onto San Jose Soquel Road, but there are a number of intermediate turns. You might also try downloading Klimb from http://www.klimb.org and seeing what route that gives you.