Commencement

I have been saying for years that one day I want to buy a "big" boat, retire, and go sailing.  I have read in more than one place that preparing yourself and the boat is a 3 to 5 year process.  It is time to start looking for the boat.
My first adventures of sailing beyond the 10,000 acre lake, where I have been sailing since 1999, is to sail the American Great Loop. 

Since I am a sailor at heart I am set on a sailboat to do the loop. This will of course require un-stepping and re-stepping the mast a couple of times along the way. But I think the silent movement of a sailboat along most of the 5,000+ miles of the Great Loop (not to mention the fuel savings) will be worth the little bit of trouble to step the mast. 
Draft: I have determined that a shoal draft sailboat is going to serve the purpose the best. A draft definitely less than 5' and preferably less than 4' is recommended by a couple of people who have done the loop.
Bridge Clearance: There is a bridge in Chicago that is a fixed 19' and the Erie Canal has a 15.5' fixed bridge (there are ways around this bridge) but since the mast will be stepped by the time I reach these bridges, I only have to worry with the other bridge heights. It looks like 48' is the lowest fixed bridge along the ICW. So I want a boat with a bridge clearance of less than 47'.
Let the search begin.