I'm mostly interested in the "dreaming" kind of planning. Just figuring out if it's even remotely possible for me to get somewhere in a reasonable period of time. I realize most people enjoy sailing for the act of sailing (and so do I; that is the primary reason I am getting a boat), but I do still want to take it places, not just sail around in a circle all day and go home. I like several of the options you guys have given me so far. I'll have to see about installing Google Earth on my computer... I run Linux, and last I checked (over a year ago), they didn't have a Linux version, but maybe they do now.
As for the trip home if I bought that boat I mentioned, I hadn't give it a whole lot of thought as I was looking for a tool to assist me. Initially I didn't think it was possible to get to the ocean from there, but my broker suggested I could go down the Hudson, out NYC and up the coast to Boston. Looking at the maps, I don't see a navigable connection between Lake Champlain and the Hudson, so I'm not sure what he was talking about... the St Lawrence might be the only option.