Hurricane season hits its peak in the Caribbean in September, but while the odds of your vacation being affected by a tropical storm or hurricane are greatest during this month, the overall danger is small. For example, the National Hurricane Center says that while September travelers to Puerto Rico have an 8% chance of encountering a hurricane, that's only if you spend the whole month there. So, if you only spend a week, the odds of a hurricane hitting are just 2% even in the heart of storm season.
September temperatures typically range from about 77ºF to 88ºF, and summer humidity levels are still present on many islands. Average days with rain in September: about 12.
Visiting the Caribbean in September: Pros
Low-season rates are the biggest attraction, plus warm, mid-summer temperatures throughout the region even as things begin to cool in the northern latitudes. This is a great time to travel if you don't want to share your resort with kids, who are all back in school by now.
Visiting the Caribbean in September: Cons
Some destinations may feel a bit "dead" at this time of year, and not every attraction may be open. For Bermuda, however, September remains high season. Tropical storms and hurricanes are the biggest negative about traveling to the Caribbean this month, although you can hedge by traveling to the Dutch "ABC" islands or Trinidad and Tobago, the southernmost destinations in the Caribbean and generally considered outside the hurricane belt.
What to Wear and What to Pack
Loose-fitting cotton layers will keep you cool during the day, especially on islands where the climate is more tropical and humidity can be an issue. Don’t forget a swimsuit, plenty of sunscreen, a hat and sunglasses. It also would be wise to pack some rain gear, just in case.
You’ll want dressier clothes for visiting nice restaurants or clubs -- and bring more formal footwear than just flip-flops and sneakers.
September Events and Festivals
Not much happening in the Caribbean during September, but there are a few good choices, especially if you like to fish. For more details, check out my article on Top September Caribbean Events.