+1 on the good plan.
I have a similar plan except for the circumnavigation part of it (yet), mostly cruising the Great Lakes in the summers. I am looking at some sailing schools here on Lake Michigan and would like to start them this summer. My kids are a little young still to take the courses, so it will be just my wife and I, whatever becomes of it, I see it as good quality time together.
I am also looking for a small boat for honing technique that I can use at my in-laws lake (found a pretty good deal on an Oday Javelin 14 that I will take a look at) and hopefully get the kids interested that way, and by spending weekends chartering.