Cruising charges/cost questions

[kkugley]

So, I've been cruinsing this forum for awhile and I'd like to ask some questions that I haven't seen answered. I'm in the research phase of possibly cruising a catamaran for several years and maybe making it a liveaboard later. I saw some guy get reamed the other day about sailing to Tahiti, so let it be know that I've already signed up for sailing lessons and I'll wait plenty long enough before I start pushing my limits.
So, I'm thinking about purchasing a 40-45' cat in the $300,000 range in FL and then island hoping in the Carribean then heading down to South America (Buenos Aires in particular). This is still a long ways off.
I've seen post talking about how expensive it is at marinas. What's to keep me from primarily mooring or anchoring and taking my dingy in to the marina or even public beach for that matter, free of charge (small charge for marina dingy I guess)? I've also done some research on marinas in So. Cal. and the waiting list is like 5 years. Can't someone just move up and down the beach from week to week or are you hassled by some authority? So. Cal. would be after I run out of money from cruising for 2,3,4 or more years. I would only do this until I could get into a marina of course.
Also, once in the Argentina area I would like to get over to Chile, but would either have to sale around "the horn" or come back up to the canal. I think I read that the canal has a long wait and is very expensive. Has anyone ever heard of trailering a yacht over the Andes? Expensive if not impossible I guess, just wondering.
After spending several months in Chile I would like to end up in New Zealand. I know the South Pacific is "sick", so I would imagine I would come back north from May-August around Mexico, then head over to Hawaii and the down, island hoping as I go.
This has been a dream for about 12 years and I'm finally in a financial position to make it happen. My main objectives are to 1.."take it easy and cruise", 2...party while island hoping, 3..surf in amazing places around the world..4 whitewater kayak (the Andes, New Zealand, Corsica, ect., as this is my current passion). Oh yea, anyone know about how long the trip from San Diego to Maui would be (estimation)?
Any other advise would be great. Again, I may sound dumb, it's because I am "sailing dumb" at this point, that's why I'm asking the questions. I can't wait for my week long class in December.
Thanks,
K

[Ex-Calif]

I read a book about a guy with a really small boat and he was basically bumming around South America. I rmember one bit where he had the boat trailered to the head of the Amazon or something and he sailed/drifted down. He was basically living like a homeless guy on a clapped out 25 footer or something.

Anything is possible - With limited experience I think it is reasonable to spend time in the islands getting to know what it is about before venturing further afield.