Have not encountered much of this in the West Carib at least. There is "Garifuna Settlement Day" in Belize
which is kind of fun, but I'm guessing not the level of historical accuracy you want. And, we do have one guy who wanders around here on the Rio in pirate custom full time.
Certainly loads of interesting history
in the Carib. You could always start something up. Cruisers would likely participate in anything to do with pirates and grog!