Lots of folks go to the Bahamas
with no insurance. Also would note that checking at a place like Morgan's Bluff where they don't normally come to your boat, in fact they may not eve look at it, as opposed to Nassau
where they might board is common in the Bahamas. Also would note in the Bahamas the length of your cruising permit
seems to vary depending on when (time of day) and where you check in. Been told Cuba
does not ask for insurance. As others have posted if you anchor
, or in some cases take a mooring
ball it is different than if you go to a dock
in a high end marina.
So to answer your question in two words, it depends.