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Dude... get a boat soon. Spend some time learning it, and then take off. Yeah, you SHOULD learn on someone elses boat. Maybe you SHOULD take a bus down there. Maybe you SHOULD spend 3 years learning how to sail, and your boat. (never should you take a cruise ship there though... you don't seem like thats your thing).
But... I think you should just go do it. If you want to sail, and your honest about things, and what it will take, then do it, and tell everyone how you did that.
How much better will it be to tell the stories of sailing down there, than of taking a cruise ship there.
There are people who would love to help you sail down there, some will want some money, but I bet there are enough around who would do it for free. You may want to hit up some backpacker websites, and see if you can find some backpackers to help you sail down there. They are a resourceful bunch.
While not as intense as a trip your talking about, I delivered my boat from NJ to VA with 3 friends. I had never sailed before, none of my friends had either, the boat had been mine for about 4 hours, it had been in the water for about 12 hours, and the broker, and PO couldn't tell me anything about the systems on the boat. We had an AMAZING trip... it was awesome.
Dude... do the trip, and post some logs here, so atleast I can read about how awesome of a trip it is.
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