"Brian Whatcott" wrote

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.

Brian - It is sort of that kind of question

No easy way to get to Caribbean proper. The Bahamas are not technically part
of the Caribbean, but you could possible get there. To do that, you would
most likely be advised to wait it out at the south end of Key Biscayne (off
Miami) until a flat calm is forecast - then motor as fast as you can across
to Cat Cay or Bimini where you can check in - I forget exact distance, but
it is something like 45 miles. The rest of the Bahamas are still another
couple of days away, so you would probably stay put and just explore the few
islands around Bimini before heading back in another flat calm.

I am not joking - the Gulf Stream passes between Florida and the Bahamas and
this area is no place to be in a small boat in any sort of wind.

You may be better advised to just poke around the Florida Keys which are
just as worthwhile to visit. OR get a bigger boat!