California to HI? Never sailed before?
Good grief! I'm an itchy trigger finger away from buying my first boat - a 28ft pearson triton - and just the thought spring launch and moving her from the marina where she is to where I want her is almost enough to give me hives. And that is literally just a 2 hour motor.
Get on some boats, sail them. See if you like it. See how prone you are to motion sickness. See if you can take the cramped cabin. Start to learn what moving a boat from point a to point b requires. There are so many little critical details.
The biggest problem you have right now is that you don't even know what you don't know. I'd suspect after 6 months of sailing you'll start to have an inkling of the right questions to ask.
Good luck! and fair winds!