...while in a marina in Presque Isle in northern, Michigan. I was in my 26' amateur built, wooden sailboat, on the fourth day of a trip up the lake and back. He had just finished dumping 1500 gallons of diesel fuel in the biggest Chriscraft power boat I had ever seen (about 65' or so) and told me that he and the skipper made the trip from southern Florida to Lake Superior in Wisconsin and back every year. Took six weeks to two months to make the trip each time, depending on the weather. They had done it six years in a row, as the skipper (owner) was retired from a job where he had made a ton of money (they spent more on fuel at one stop, than I had paid for my whole boat!)
Was an interesting, unassuming fellow, who wanted to talk about my boat because it was different than all the other boats at that little marina.
Sounds to me like it would be a great adventure!