Another plan would be to develop a skill that other boaters need. Suppose you learned to be a diesel mechanic. You could make money fixing other peoples boats..
I like this idea a lot. This requires about 2 years of school though doesn't it? Not that I'm opposed to that idea, just trying to gain an understanding.
Also, my current profession is in video/film production. I wonder what the market would be for a videographer to travel with cruisers and document their adventures??? anybody??