I've been considering moving somewhere on the coast of Lake Michigan, and recently I've fallen in love with the idea of going on a long sailing voyage from Lake Michigan to the Bay of Fundy, or possibly beyond if I become experienced enough at sailing that I could pull it off.

I'm wondering if anyone around here is at all familiar with sailing, or if I should maybe ask on /trv/ instead of something, but I want to know if this is really a realistic goal to have, I'm from a landlocked state (Missouri) and while we have the Mississippi and a few man-made lakes, sailing isn't the biggest hobby around these parts.

One of the main things I'm having trouble with finding is recommendations for the kinds of boats that would be appropriate for such a journey, how big of a boat would be too big, how big of a boat would be too small? Could a vessel suitable for the Lakes and the St Lawrence also be suitable for the Atlantic or the Gulf of Mexico?
While my goal is making it to the Bay of Fundy, could going to the Caribbean or even docking in Europe in the same vessel be a realistic endeavor to pursue, or should I not set myself up for the disappointment of discovering such a journey to be unfeasible?

Please pardon my ignorance on this subject, but you have to start somewhere, right?