1. Ask your airline about its hurricane policies. Will your ticket be refunded?
2. If you become stranded, how will your airline help you? Find out ahead of time.
3. Will your deposit for a prepaid room be refunded?
4. What are the city/island/resort's evacuation plans? Are there hurricane-proof facilities for tourists?
5. What are your options once the storm hits? The city of New Orleans learned a lot from the Katrina disaster and now has a master evacuation plan in place, which includes a partnership with Amtrak.
The Caribbean Tourism Organization does not have any organized evacutation plans at this time; it's best to check directly with each island's tourism office.