When my wife and I went on our honeymoon 11+ years ago we went to a Sandals resort which is all-inclusive, including Hurricane Insurance. Well, as luck would have it, we had to leave on our 6th day of our 7 day trip because Hurricane Georges was bearing down on us (Antigua). Their insurance stated that if any part of our trip was interupted by a hurricane, we would receive a full replacement vacation for the same length of time our full trip was supposed to have been. We were lucky and able to get out before the hurricane struck, but we had to go back and forth with Sandals for a little bit to get our replacement vacation. Ultimately a letter was necessary but we were back at another Sandals (St. Lucia) 8 months later (had to use it within 1 year). At first they said we had to basically "survive" the hurricane to get the replacement vacation but after mailing a letter there were no questions asked. As crazy as it sounds, my wife and I thought we were quite lucky.
Felt bad for the good people of Antigua though.
We met a few couples in St. Lucia that did rough it through the hurricane and it sounded pretty bad. They ended up getting flown out in a private jet (Sandals owner is a part owner of the Heat I think?) which sounded like the highlight of the whole affair.