In the 18th century being sent to the Caribbean meant that you very likely would never return home. Let's put the prettiful pictures of the movie aside for a moment: the reality was dirt, illnesses and killing heat. In one scene cut from the first Pirates of the Caribbean movie, you can see Elizabeth and Gov. Swann in a coach, and he's praising Norrington for his great achievements in "civilising" Port Royal. At the same time, you see people sitting in the mud and the "real" face of the place.
Means: it's highly unlikely that the "elite" would have been sent to the Caribbean. The elite was kept in England, away from malaria and typhus. So all the main characters in this story do have a skeleton in the closet. Maybe not a big one, but one that's rattling its bones from time to time.
With exception of Lord Cutler Beckett, who very likely has his own private ossuary.
While "The Joyful Molly" is fan fiction and doesn't want to do more than entertain, I did quite a bit of research and tried for realism where appropriate. The Caribbean wasn't paradise, and the characters no saints. Which is a good thing - how boring if they were!
by Molly Joyful