Thanks for the replies, folks. I havnt been to Lake Jericho since I was a kid. So of course it seems much bigger that it likely is in my head! However I DO recall sailing lessons there in small sailing dinghies, so that is likely what I will do at first.
I have BEEN sailing before, I have just never done it myself. A few of my dives took me out on a sailboat, and I have looked at a few here in Winthrop harbor in Chicago.
I took out a pearson 35, well, the person selling it took me out on her. I was looking at them because they're much bigger than the bayfield I went out on for half the price. Boy did I see why. The interior wasn't as pretty, and soon as the wind picked up I thought I was gonna die. Never been on a boat when it heeled over like that!
Anyway, I will likely keep everyone apprised of what I do. As for my plan, I am going to spend the next year saving and learning all I can! Then I am going to find a 29-32ish foot boat and go to it. Doesnt matter where it is, I'll go to the boat, stay around there for 6 months or so learning all about her, then take her to the keys