My wife and I are also contemplating this same question. Our though process so far is;
Florida gulf coast-nice sailing but a long way to sail before you start sailing somewhere farther. Lots of places to sail to in the gulf area for local sailing and protected waters Nice water
. Definitely hot in the summer. No seasons.
Florida east coast
. Great starting point for lots of longer destination
sailing and Bahamas
. Same weather pluses and minuses as the gulf side. Not much local destination
sailing and no protected waters to sail in.
North Carolina-Seasons which means a little more winter than I would love but still not too bad. And seasons are nice change of pace. Great local destination sailing and close to the Chesapeake Bay
. Water is not so pretty and colder. Protected water in the sounds.
Looking online at houses I also like the feel of the houses in NC a lot better than Florida. It appears that in Florida to live on/close to the water and not in a condo you have to spend well north of 500k. I am not sure if I am ready for condo living. I still like to have a little space around me and a place for tools and stuff appeals to me.
Who knows where we will end up. Currently we will most likely rent a place and live for 6 months to a year and then do the same in the other place before we commit and purchase
a home. Hard to really know without actually spending some time.
I will be interested to read everyone's commits/thoughts