I grew up in the Santa Cruz mountains, just outside Los Gatos and think castle rock state park for example is amazing. One the best hikes is from castle rock through big basin down to the beach. Takes about 3 days to get there and so long as you have someone to pick you up at the beach it's pretty easy going.
[edit] from Los Gatos, Castle rock is 10 minute drive if your used to black rock road otherwise 20 minutes up highway 9
[edit] from Los Gatos, Castle rock is 10 minute drive if your used to black rock road otherwise 20 minutes up highway 9