I really love sailboats and I'm interested in getting into sailing; I'm just wondering how much you can really do with a sailboat in the 18-23' range (I'm thinking in particular of the respective Catalina models).<br /><br />I read on another site that people have taken 18 footers from California to Catalina Island and as far as Hawaii. Do only people who have been sailing for 25+ years do this? This seems like a stretch to me, but what exactly makes a smaller boat bad for ocean going. Is it high winds, a light/tossable size, what?? Is the Pacific "nicer" than the Atlantic (in general)?<br /><br />I live in Virginia and would be trailering a boat and have a notion of sailing in the Chesapeake Bay. Do people sail to places like the Bahamas and Prince Edward Island often, and if so what's the "recommended" size minium (and experience minimum) for such an excursion? Obviously I'm not thinking that I'm gonna run out and tackle an ocean-going adventure out of the box, so to speak, but I just don't want to simply sailing around a "bathtub" all day. I assume something like crossing the Chesapeake to the Eastern Shore would be totally doable for a boat in the 18-23' range, right?<br /><br />Sorry for machine-gun-like questions. I'm about to go to the book store to read as much as I can about all this stuff. It's been frustrating finding adequate online resources for such info. Thanks in advance for the help! 