This article by journalist and cruiser David H. Lyman (Jan. 2021) has lots of helpful information re. health insurance if cruising the Caribbean.

This is a useful comment about repatriation insurance - posted on the Seven Seas Cruising Association Facebook page:

As a retired physician who cruises full-time...6 years in the Caribbean followed by a Pacific crossing, I tend to get involved in other cruiser's medical problems. Even in the Caribbean medical care, at the higher levels, is very spotty. Ok for minor stuff but not for major problems like heart attacks. I have organized 3 medical evacuations back to the US, 2 for problems that were potentially life-threatening. I think that the most important insurance to carry is repatriation insurance...
We have Divers Alert Network repatriation insurance that not only covers us for scuba dive accidents but repatriation or transportation to a first-world hospital for non-scuba problems. One friend with cardiac problems was flown by Lear Jet from Bonaire to Miami and arrived in Miami within 15 hours of my initial contact with DAN. Fortunately, my friend had Medicare to cover the very expensive cardiac care that would not have been available in 95% of the Caribbean. Our DAN insurance (you do not have to be a diver to purchase), cost us less than $200/year...the Lear Jet cost $28,000, no deductible!