What happens if there is a hurricane?

buy a flight ticket with the most flexibility to change (and these are the most expensive)
buy travel insurance that covers acts of god if possible.
or use the saved up vacation time in the winter when there is little chance of hurricane

Having "ridden out" a November hurricane on Kauai, I can say that it was a memorable experience -- after a few scary hours of intense wind, we had several days of no power but the condo manager provided candles for nighttime light, the radio station broadcast news about what companies were open, and different restaurants were serving meals using their backup generators.

On another (September) trip, I left New Orleans just before a hurricane hit -- I already had confirmed reservations, but the airport was crammed with other people trying to get out ASAP and the highways were jammed. So I would guess that once a hurricane is imminent, getting off an island may be difficult, if not dangerous.

Given your time frame and destination choices mentioned, Hawaii is the better choice for having the better statistical chance of avoiding a hurricane.

If your travel time is fixed and you are concerned about hurricanes, you should look at other destinations.

I wouldn't worry too much about hurricanes in Hawaii - I did experience hurricane Iwa in Nov. 1982 during a 3-week stay in Waikiki (Honolulu, Oahu). There was a day of high winds and heavy rain, and a few days without power, but the visitor industry managed just fine. Although it was slightly scary with no power (we all had flashlights and transistor radios - remember those?), everyone stocked up on non-perishable food, water, etc. to ride out the storm indoors and the weather was beautiful once the storm had dissolved. I never even considered flying home to Canada when I heard the storm was coming - it's really quite rare in Hawaii. I've been to Hawaii six times between September to November (as well as umpteen times December to February) and that's the only time we had a tropical cyclone. Ten years after Iwa, there was a hurricane that hit the island of Kauai and I missed that one with the timing of my trip.

Parts of the southern Caribbean were historically not in the hurricane belt - Aruba, Bonaire, Curacao (not sure about Trinidad and Tobago). However:

1) I have not idea if this is still the case. Hurricane patterns have definitely changed in recent years.
2) I don't know if these islands have what you're looking for. For instance, Bonaire is supposed to have great diving, but not great beaches.

I do know that, about 15 years ago, my sister and her husband were thinking of taking a September honeymoon in Puerto Rico - until they learned this was the height of hurricane season. Like you, the thought of monitoring the weather report every day, and worrying about possibilities if one was to hit, wasn't their idea of a vacation. They elected to go to the Big Island of Hawaii instead, and had a fantastic time.

And among others don't make jokes about hurricanes. When I still lived in small town Hanover in Pennsylvania my friend came to say good bye because he was moving to St.Croix in Virgin Islands. We were joking about hurricanes which was probably a mistake at least for him. In two weeks he was back because hurricane destroyed his house in Virgin Islands.

Ok, thank you for your insights. Sounds like trying to get off the island may not be feasible on the rare occasion that a hurricane hits while I'm on one of the islands. Unfortunately, because of my family's schedule, we need to travel at the end of August/beginning of September, so it will be a matter of deciding whether we are going to risk it on an island or choose another type of destination. I'm assuming that most places in Hawaii wouldn't be equipped with official storm shelters (the type that nearly guarantee safety), but rather the plan would be to get to the safest possible part of the hotel and hope for the best? I don't know a ton about hurricanes since my part of the country doesn't get them, but I'm thinking that if we may have to choice but to ride it out, we may need to pass.

You do not say where you live but I suspect there is some adverse weather or force of nature that could strike. Be it earthquake, tornado, blizzard, flood , fire or whatever, every where has some hazard.

I suspect you live someplace where hurricanes do not strike and you seem to be obsessing over it because it is an unfamiliar thing. I also suspect your area is subject to some sort of natural disaster that you have learned to live with.

Your thought to choose a destination other than a tropical island is probably a good one, and will give you peace of mind an let you enjoy your trip, rather than be in a constant state of worry

Yep, I live in earthquake territory, so that's just something we just have to live with. We haven't avoided traveling places with earthquake or tsunami risk, since those aren't predictable and there's always some risk everywhere you go. However, since hurricanes can generally be avoided by going out of season, it feels much less stressful to me to just go when it's not hurricane season. Even though it would be more convenient to go this fall, the point of vacation isn't to fret about the weather (we've been in spots before where we have to decide last minute whether to cancel a trip, and it's not fun), so we'll probably just wait and go next spring if there isn't a good way to evacuate on the rare chance that a hurricane happens. Don't mean to "obsess" about it, just want to make sure I understand what is reasonable to expect and make a decision that feels the least stressful, as it doesn't sound fun to me to ride out a hurricane on vacation when I could have just waited a few months to visit after hurricane season is over. Appreciate everyone's input!

If I had to choose between your destinations, I'd go for Hawaii. While there's a good chance active hurricanes may not come anywhere near whatever Carribean island you may be leaning towards, you really get zero assurances because the storm path can change overnight leaving you a sitting duck. My mom used to have a habit of wanting to spend a month every year in Florida during hurricane season because it was quieter and far cheaper and easier to get a rental during that time. There was a period of about 3 years in a row where they predicted hurricanes heading to the area she was staying which had us all on edge. One weakened and broke up before getting to her, another she had to ride out in a shelter until it passed because she couldn't get out ahead of the storm, and the last one she really lucked out on because it totally changed course, gained strength and slammed into New Orleans. That storm which missed her was Hurricane Katrina. That effectively put an end to her Florida trips during the hurricane season when she had all of her children join forces to say NO after seeing what happened in New Orleans.

I would look at it as a risk analysis. Based on what I have seen and comments of others, Hawaii would be a good option, or as others mentioned Southern Caribbean (Dutch Antilles, some of the western Islands.

The biggest problem with Katrina was the breaking of the levees-not an issue in most places that have hurricanes. If on the mainland or a barrier island in US, there is usually plenty of advance warning that everyone needs to leave-sometimes, all the interstate lanes are converted to outbound. Messes up your vacation but not dangerous if you listen to the authorities and leave before the hurricane's arrival. I consider earthquakes and tornadoes much scarier.