I used to take the trails by the bay from the Googleplex to North San Jose - most is unpaved gravel, and then you pass by a smelly waste treatment plant and get on some paved trails. Even on a hybrid, it was not the most pleasant cycling.

Those were at least dedicated bike trails, which is more than I can say about a lot of other areas in South Bay. I would never attempt to take Shoreline over 101 and compete with all the drivers trying to get on the highway on-ramp.