We used to go a LOT during September/October timeframe and I thoroughly enjoyed the uncrowded aspect of the island at that time. We have been lucky enough to never have had any problems with storms while we were in the Caribbean, EXCEPT for 1999 for 'wrongway Lenny', when we had to be evacuated by AA from St. John, USVI, ahead of the storm. And Lenny was in NOVEMBER. Go figure. Now that we live in Florida, the bigger problem in the back of my mind is if we were to have a hurricane HERE, while we were gone.