Wanted: A Sensible First landfall in the Caribbean for Inland Sailers.

My son and I would like to take a baby step offshore from Florida to a
Caribbean destination, in fair weather, aboard a SouthCoast 23
(A trailerable centerboard sloop) as a first voyage, next Summer.

I hope that this is not a question of the kind that if you have to
ask, you shouldn't be doing it.....
I would appreciate any and all advice on the topic.

Thanks in advance.

Brian Whatcott Altus OK