[PalmettoSailor]

You didn't really say what you were looking for in terms of a sailing area, but since your proposed window will fall right into Hurricane season, I'm guessing maybe not the Carribean unless maybe you consider xort's plan (which actually sounds pretty cool to me).

Anyway, if you are set on buying your own boat to do this, how about the Chesapeake Bay? There are tons of boats available for sail and you could easily spend a couple of months just poking around the bay. If you get tired of the bay, you could head south down the ICW and end up closer to home. Also there are many, many places on the bay capable of addressing any unexpected issues that might come up with the boat.