I am from Indiana's sturdy farming crop. My family had one of the best dairy herds and hay crops in the nation for years (my great-great uncle was the international "Hay King" seven times). That said, it seems pretty clear that I would know little to nothing about water-based anything. I've been to cottages on lakes in Michigan, and I've been in both the Atlantic (a lot) and the Pacific (once) yet I've never learned anything about the art of sailing. For some reason, I'd like to.
I've been windsurfing once on the Hudson. I also have relatives who live right off of Cape Cod. They are older and have never been water-sporting types. That area, however, has a remarkable pull to me. I don't know if there's just something in me that likes the preppy, aristocratic, I-don't-have-to-do-anything-since-I'm-rich-so-I'm-just-going-to-learn-how-to-sail-with-my-overly-abundant-free-time lifestyle (read: Kennedyesque) or if I would actually enjoy the ocean.
Two nights ago, instead of watching the Super Bowl (I don't have a TV...), I read The Old Man and the Sea by Ernest Hemingway. It is a quick read (only about 120 pages). I haven't had much time to think about its significance or to interpret the old man's resemblances to Christ as He's crucified. Something that stands out to me, though, is Hemingway's excellent ability to describe the world of fishing and of life on the sea. From his descriptions of the barrel of shark oil that the man drinks out of every day to the lavender and silver stripes on the marlin that he catches, in many ways, even for a drylander like me, it makes me feel like I'm there. The smells and taste and texture of the fishes' meat make you want to throw up, just as the man wants to. It's worth the read.
I'm afraid that another reason that I am interested in sailing is because of boat shoes, particularly the Sperry topsider. Pathetically, I already own four pairs of these shoes (plus an old pair from the 80's that my dad gave me). I wear them instead of sandals, since feet gross me out. Topsiders are not only cool looking, but they are practical (apparently on boats, because of the grooves; that was their original purpose) and machine washable. You can get the shoes wet and disgusting, but then wash them! They're made for it!
This year, there are two new ones that look awesome. Both are plaid (what can I say?), which should match your handy, preppy plaid shorts.
So, from the mouth (keyboard) of this midwestern boy: go out, buy boat shoes, learn to sail, and enjoy the sea! Of course, you have to wait for that bane, winter, to be dispatched first.