Goal is to learn about sailing and how to while maximizing usage and fun. I learn by doing. I have triple digits to invest. The first thought is to get something like a cal22 used and just refresh it. Then I started wondering and doing research. It would be easier to have something I can just roll out to the beach.(its a block away) Something as large as a cal22 would require a slip or to tow. (I can not tow) (nor do i have extra money) Dinghy I could carry / roll by hand < is going to be most practical in my situation. Dinghy I can also capsize and self recover, as I am getting involved independently. Here is my next issue. I would like to be able to relax/sleep/nap on it. I came across an article talking about camping and such ashore on a dinghy. Witch sounds great for maximizing usage. I would like something room enough for that and supplies for self sufficiency. The most probable things I've came across Canoes, Kayak and Dinghy. The cheapest are Canoes. They are not fitted to sail, but I can outfit it myself. (within budget) Honestly that would significantly increase my expertise in the subject. << the way I see it. That brings us to the point of topic, what are some more experienced opinions on this?