We have never purchased any trip insurance. Usually in the winter when we go there aren't to many problems. We have traveled for many years to the Caribbean with no issues. I'm sure one day we will get burnt but we will just deal with it at that point. Anyways in the "what is it worth department" we don't ever buy any extended warranties either.

On a side note I have now figured out that one trip in February is not going to be enough for us anymore. I need to find another spot to get away for at least a week or so. I was thinking in January but that letter I just received from the "Clerk of the US District Court Jury Department" has notified me that January is out. So I might have to figure something out for March. Anyways we are always looking for some good information on Caribbean destinations if anyone has any advice.