>>246439OP is that a pic of Rainbow? Or maybe another J?
Anyways I love sailing, mostly in sunfish. I recommended looking into local yacht clubs nd see if you can take some sailing lessons or something. Joining a yacht club is your best bet because it will give you access to boats without having to buy one, and you'll probably have more than just one boat to sail.
However, if you really want to buy your own boat, I'd recommend a sunfish. Its a great, simple boat that can be a blast and a challenge for anybody. (see vid)
You can also see if there's any big keelboat racing fleets around you. You can call them up and see if you can get a ride on one of their big expensive boats.
http://www.youtube.com/watch?v=59RS9sT8S-U 