I rode something similar about 10 years ago. I was in Campbell, in my early twenties, and bored with work and Campbell in general. So on a whim I took off out of the garage on a 3 day weekend. Of course none of my buds would come as what I was doing would take actual work.
All I had was a a little bit of money, a map, a sleeping bag, and some very basic eats, all on a back rack.
I rode up past Lexington reservoir late in the afternoon and raced the sun to Summit road. Did I mention I was out of shape? I figured I would get in shape on the way (that didn't work out too well). I slept just off of Summit road, just before the land slide covers it. Woke up in the morning just above fog line, beautiful.
Then travered the land slide and continued on the road past the illegal shooting range, with assorted appliances etc. Cue banjo music. Then rode up to the back of a long park I cannot remember the name of (Niesene Marks?) and wheeled down the fire road for about 9 miles and came out near Capitola. Grubbed a burrito on the bearch and started riding north to Gazos Creek along hwy 1.
Note that wind off the ocean will be in your face when riding north. The whole way...
Well I broke some spokes on the way, ran out of water, but made it and camped on the beach. I thought it would be glamorous sleeping on the beach, but it is a harsh evironment. Wind, bugs and high tide kept me awake.
Next morning I woke up, begged someone for water then rode up Gazos Creek road (?) and into the back of Big Basin. Rode fire roads throughout Big Basin popping out near hwy 9 and back up over Summit Road. This day was the hardest, as I was fatigued, sun burned, wind burned, out of food, out of money, and running out of water and it was all up hill on hwy 9. Ping, ping, more spokes breaking. Being in my early twenties, meant that having proper tools for the ride was out of the question.
I earned Summit Road and to reward myself bombed down hwy 9 towards Saratoga. by this time I had lost 4 spokes and my rear wheel was so out of true it was almost rubbing the stays (1.5 tires). Zoom! Ping! Another spoke gone. Zoom! Ping! Ok, slow down.
The rest of the ride was mellow and about savoring my acheivement.
It was an eye opener for me. I changed on that ride. Discovered things about myself and about the generosity and warmth of strangers. It was truely epic for me. Adventure can be had at home.
A huge help is the Bay Area Bicycling map (dunno the name), it can be bought at most bike shops. It shows the traffic density of roads, MTB open fire roads and trails we can ride as well as the gradients of the hills.
As Henry Rollins says (screams):
DO IT! DO IT! DO IT!
Mr. P