Having spent half my working life as a yacht carpenter, and sailing the Chesapeake Bay both racing (a Beneteau 39) and day tripping, I'll second the motion for starting out with a one-man day sailor. Learn the basics, have fun with it, immerse yourself in the "sailing culture" and then decide where to go from there.
Having been on blue water when heavy seas were threatening to kill me, believe me when I tell you that no boat will seem big enough under those circumstances.
I can't resist the old adage: "The two happiest days in a man's life are when he buys his first sail boat and when he sells it!"
