I sailed Michigan's western shore, from Chicago to Mackinaw Island and the Abacos Islands in the Bahamas extensively. With the question posed, it didn't take me long to realize the answer. I moved to Florida later that year and joined not one but three SW Florida sailing clubs. I began to charter and race extensively on all kinds and sizes of boats in club and interclub regattas in the tranquil waters of the Gulf of Mexico. Since those early days I have made and learned by innumerable mistakes.
Most sailors do it seems.
I have been in gales, tropical storms, hurricanes, have had rigging fail, rudders break, engines quit, sails tear, and been hard on reefs. I learned over and over again the critical importance of vessel preparation, navigation, and weather. In 1985 I became certified as an ASA, Advanced Coastal Cruising Instructor and began teaching sailing professionally. I usually average 7-10,000 sea miles per year. Since 1985 I have logged thousands of hours and thousands of miles, sailing all kinds of boats around Florida, the US East coast, Gulf of Mexico, and Caribbean.