OK folks, put aside your advice about lifestyle and criticism of "commuter cruising".... I'm not ready to retire and cut the lines. The question is about where to leave a boat and when?

I'm thinking maybe in a year or two of taking the boat south to Florida and the Bahamas for the winter, and visiting the islands for 2-4 weeks at a time. Is that viable logistically, in terms of safe places to leave it in the Bahamas where there are good air travel connections? Any government issues? Of course we could find a place to keep the boat in south Florida and hop across to the near-Bahamas once in a while but we could go further if there are good places to leave it there.

Advice on whether that is practical?