Regarding travel insurance, you need to look at the limits on the various policies and what types of perils you are most interested in covering. I am not necessarily that worried about Covid coverage now, as coverage for regular medical expenses and medical evac. But some things, like cancel for any reason insurance, have to be purchased within a very short period of time from when you made your initial payment, so if you're outside that window, you don't need to worry about that. Also, on medical insurance, I look for PRIMARY coverage, not secondary coverage. That is what is very important to me, because my Medicare Supplement has only partial coverage for medical costs outside the US, and I don't want to have to shell out extraordinary amounts of money and wait 6 months for an insurance company to pay me back. For the actual cost of the trip and trip cancellation, those aren't that important to me for a trip to SXM because I could probably get my money on that applied to a future trip for the hotel and the airfare probably I could get refunded. Your mileage may vary.