Hurricane Season in the Caribbean lasts from June 1 through November 30. Although it's rare to see a large storm in either June or November, you can never be sure what Mother Nature is going to do. Here's some helpful information on how to weather any storms you might encounter while traveling in this region.
Airlines
If you are scheduled to fly into an area where a hurricane is expected, get travel updates from your airline. If flights are disrupted, airlines will usually allow you to rebook at a later date, but you will not get a refund if you have booked a non-refundable ticket, nor in most cases will you be allowed to change your ticket to a different destination; rather, you will be expected to reschedule your trip for a later date---most often without any kind of change penalty. Some airlines will waive change penalties when a hurricane is a possibility (though not a certainty) so you can rebook your trip in a limited period of time; this gives you an "out" to avoid a rain-soaked vacation you no longer want to take (airlines do this so they won't be bringing a lot of travelers into an area that they might have to evacuate later). If you find yourself stuck on an island during a hurricane, just be aware that your departure may be delayed while aircraft are flown in to deal with the backlog of tourists trying to get off the island, and since the delay is weather-related, the airline will not be reimbursing you for any additional costs, including extra hotel nights, restaurant meals, or telephone calls back home.
Hotels & Resorts
Caribbean resorts do everything in their power to protect guests during a hurricane, but don't be surprised if you are asked to stay in your room or to sleep in a public room during a storm. Food service may be limited, but most resorts go out of their way to keep guests fed and reasonably happy. A particularly destructive storm can make that a challenging proposition, however. If a hurricane warning is issued and flights are disrupted to your destination, virtually every Caribbean resort will waive cancellation and change penalties and will allow you to rebook your trip for a later date; some will allow you to cancel even if a hurricane threatens to strike, even if flights aren't scheduled. Some will give you a refund if you have prepaid for your stay, others will expect you to rebook your trip for a later date. Some large resort companies---including Sandals and SuperClubs---have "Hurricane Guarantees," but these kick in only when flights have been cancelled or when a hurricane is sure to strike; just remember that the guarantees give you a credit only for the days that were directly disrupted by the storm. If there was rain for two days before the hurricane actually struck, you won't be getting any credit for those. On the positive side, if you must stay a couple of extra days before a flight is available, most of the hurricane guarantees will cover your lodging costs for this time. If the resort is not an all-inclusive, you may still be expected to pay for meals and drinks.
Pre-Paid Packages
There's nothing more disappointing than pre-paying for a package deal you can't take because a hurricane is bearing down on the island. Travel companies have different philosophies about this. A few will refund your money if a hurricane is about to hit the island where you've booked your vacation, but you should expect the refund to take at least 30 to 60 days. Most will force you to reschedule your trip. Even if the resort you've booked has a hurricane-guarantee policy, you may have to fight for your 2 or 3 days' refund from the travel company, though most will make good on guarantees, though they might not do so efficiently or happily. This is where a good travel agent comes in handy; your agent can work on your behalf directly with the travel packager. If you've booked your package online, you'll be fending for yourself. If your travel company has its own policy for weather-related cancellations, that policy might also allow you to rebook for a different date, but you'll still rarely get a refund.
Travel Insurance
Doesn't travel insurance protect you during hurricane season? Yes and no. Most travel insurance policies will cover a trip disrupted because of a hurricane (when you are forced to arrive late or leave early for your trip), but you'll be reimbursed only for the affected days until the airport or resort reopens. You will usually be reimbursed for the days you are forced to stay at a resort during a hurricane, but be sure to read the fine print on your policy to make sure you are actually covered. And remember that you'll usually only be covered if you buy your insurance at the same time you book the trip or before any kind of hurricane watch or warning is issued; otherwise, the hurricane might be deemed a pre-existing condition, which means no compensation for you. But if the airlines are operating and allowing passengers to fly to the destination, you'll usually be expected to leave for your vacation, even if a hurricane threatens. Also, most insurers won't pay as long as the airline is flying, even if the resort you booked and paid for is totally destroyed by the storm. In a case like this, it's usually better to take advantage of the airline's more flexible change policy and rebook your trip for a different time and a different resort.
Cruises
The good thing about cruises is that they can usually sail around the worst of a storm. And today's ships are extraordinarily safe. The bad thing is that the cruise you get may not be the cruise you signed on for. A cruise line always reserves the right to reschedule port calls and change itineraries for weather-related reasons; the line might even shift a cruise from the Eastern to Western Caribbean if a hurricane threatens its route. There is almost no chance you'll get a refund just because the port you've longed to see is no longer on your itinerary. You might get a discount on a future cruise or a shipboard credit, but that's about the best you can hope for. If you aren't able to get to your port of embarkation because of weather, be happy that you bought a travel insurance policy. You did that, right?