There is wisdom in this, many Caribbean sailers leave their boats in that area and can never recover them due to health/age. Lots of deals to be had for a boat that's been sitting for a couple years and just needs a good cleaning. I've heard st maartin is the best place in the world to refit a boat aswell.There are lots of boats available in Florida.
coming South, unless you intend to take the outside route, you will likely want to leave the States from Miami.
Many sailboats wait there for a window to cross the stream.
Just thinking you can find an experienced Caribbean boat down here... ready to go.