Have you taken the trip to Monterey yet? Where in San Jose were you coming from?
When I went from Sunnyvale to Monterey, my basic route was through Los Gatos, along the Los Gatos Creek Trail to Lexington Reservoir, to Soquel-San Jose Road, then the 'coastal route' on to Monterey. All was pretty bike friendly, and relatively flat, with a few bike paths in Monterey. (I could dig up the cue sheet that I received from somebody else.)
On the way back, I went through Salinas, San Juan grade road, through San Juan, down 101 to Gilroy and Monterey Highway for a long long long long time. This was also fairly flat. The most significant hills were on San Juan Grade, and that has just about no traffic. The short stretch on 101, however, has a couple narrow bridges that are not very fun. And Monterey Highway just seemed to go on forever. (The "San Jose City Limit" sign is especially misleading.)
For this year, I am thinking about alternative routes. I wonder if summit can be taken all the way now?