Beach/island Wedding in Off Season

"I have a fear of everyone getting stuck on the island after a hurricane hits and flights are cancelled because of flooding"

That is a legitimate fear that you shouldn't ignore. Hurricanes are getting worse each year due to climate change, so it would be pretty irresponsible to disregard them when you are planning.

If you are desperate to get married on an island during hurricane season, make sure you have travel insurance (although I'm not sure if you can even get travel insurance for that) and just plan to elope so you aren't "forcing" your loved ones to be involved in your risky plans.

Agree with KK & Maggie. Another thing to consider is that what a hurricane passes before your wedding leaving your venue/space damaged or unable to be used. I lived in Puerto Rico for many years before I moved to California and hurricane season is no joke, cancelled flights, flooding, no light, water or other necessities like gas and food.

What islands are you looking at?? I'd definitely ask a lot of questions about the weather that time of year, and what backup plans look like!!

We had an all indoors wedding planned in NC and were surprised with Hurricane Matthew which still threw a huge wrench in our day (even though we were 4 hours inland!!)

Really depends on the location. We havenʻt had a hurricane here in many years so I wouldnʻt worry that much here, but other places where they do hit quite regularly, I would avoid.