Should I be worried about sailing the Caribbean late September weatherwise?

[Husky1987]

In Sept 2017, we left San Juan on Adventure while Irma was on the way.  Had a wonderful couple days in San Juan, we love it there.  Skipped St. Kitts as it was passing through there and added Bonaire to Aruba and Curacao instead.  Irma rocked San Juan and we came back after it passed.  Heartbreaking to go from ship to airport with such a stark before and after.  

[cruiselvr04]

As mentioned, hurricanes can happen 6 months out the year.  We’ve had missed ports in October and even early November.  
 

That said we don’t cruise mid August to mid September just because that seems to be the height of it.  This is really only because of increased risk of trouble getting to and from embarkation.  If driving you also need to make sure your car will be as safe as possible while you’re gone.  If you’re out on a ship they will avoid it, no worries.  We have cruised and will this year in early August and late September.  Rates reflect the risk of weather too.