We did this last season and the first thing I would say is DONT start in Florida. If you have to start in January then hop a plane to the Virgin Islands
and buy a boat there. Or have your boat moved there by a delivery captain
because if you start out by subjecting your wife and kids
to a 600 mile upwind bash you will be done before you even get to the Caribbean.
Having said that, our favorite spots on our one-season trip to the Caribbean last year were Antigua
, Bequia (and the Grenadines generally) among the English
Islands and Martinique
among the French. Rodney Bay on St. Lucia was a good and kid-friendly place for cruisers to hang out too.
We didnt get to Grenada though - Maybe next time! By the way - I also think it is a good idea to get south fairly quickly and then meander back hitting islands that were fun the first time
My return was exactly what Hud did - The sail from St. Maarten to Marsh Harbour took about a week and was about as pleasant a sail as I have ever had. From there it was a four day trip back to Beaufort
and then the ICW
back to the Chesapeake.