To the OP I say its totally doable. In fact that is my current plan. I spent the last 8 months living and sailing (mostly single handed) on my Cal 25. Prior to this I had zero sailing experience. I would recommend taking a sailing course though. They are fairly inexpensive, especially in the off season and you learn a lot. The two week one I took was only about $600, and I left feeling supremely confident, and had gained some actual skills and knowledge to boot. I'd also suggest you read some of the books by Larry and Lin Pardy if you haven't already, very educational.
As far as the boat being able to carry enough supplies, the first boat to complete a solo non-stop around the world voyage was only 32 feet long, and he didn't
use a water maker. Hawaii is not nearly as far as that. I have also done some extended wilderness hikes and have no problems carrying two-three weeks of food on my back. Seeing as a trip to Hawaii should only be about three-five weeks (from what I've read) for that size of a boat depending on speed, carrying enough supplies should not be a problem.
Its basically about having the guts to go for it. My Grandpa is 80 and he just bought his first sailboat this summer with zero previous sailing experience, now he's obsessed with using his spinnaker. I should mention though that he has owned/made a living off of and been sinking fishing and tugboats for years.
I think there's a webpage somewhere that reads, "Don't want to work anymore or have any
responsibilities.....get a sailboat, it's that easy"
Not saying that's the OP's ideology, but overall, not just in sailing, there's this thought process
that "you don't have to get a job or need to be tied down in any way" and that it's as
easy as making a decision to do so, without prior planning, etc. Most of the negative
responses come because ultimately, it's the folks "left behind" (for lack of a better term)
that will be asked to pick up the pieces and repair the damage should that plan fail.
There's also a segment of the emerging population that doesn't believe working towards a
goal makes any sense; they'd prefer to start at the end, instead of the beginning. I actually
heard a person say to me, "I could either live in a crappy apartment with a roommate, or
I could be cool and live on a boat for less money", with visions of a 60 foot yacht in his
head. Once he was introduced to what his savings of $1500.00 actually purchased, needless
to say, he was quite disappointed. He didn't care about sailing, or even boating for that
matter, it was all because he didn't want to "be like 'them'", whoever they are.
I just wanted to say that this is exactly how I think and live. Didn't want to rent a apartment so I bought a boat for $3000. In fact I thought this pretty much verbatim
I could either live in a crappy apartment with a roommate, or
I could be cool and live on a boat for less money
. Its not that we don't know how to work towards a goal we just do it differently.