We go somewhere in the Caribbean every October. As @Jeannius says, you do need to be concerned about Hurricanes by having a Plan B for a location further south. One thing not often thought about is not that there's a hurricane when you are scheduled to go, but that a hurricane came through *prior* to your trip. 2017 is the primary example. Irma did so much damage in early Sept, there were no charters available for months from Dominica north through pretty much all the islands. We ended up in Curacao.

Another note on this is to check your trip insurance. If you go with a travel insurance company there's a 30 day window after the hurricane for which they'll cover. Irma hit St. Martin on Sept 6/7. Our scheduled charter out of St. Martin was Oct 8 - exactly 30 days from when Irma hit. Initially, they did not want to cover but a short letter from my attorney took care of that. I suspect if Irma had hit a week earlier we would have been out of luck. Now we use the credit card insurance which doesn't have that time limit.