Originally Posted by cherev
Take a keel-boat sailing course, take any instruction that a local boating association or college offers, and practice lake sailing. Then bare-boat sail on chartered boats in sheltered waters like the BVI. Then do some more charter sailing on more open waters such as those in the Caribbean. You might try crewing on a boat delivery or two.
I, too, endorse this plan. By the time you have completed these courses and charters, you will be so experience rich and cash poor that you will be unable to buy anything that could possibly get you in trouble.