We usually go in September because it's our anniversary. It won't be crowded and some places my be closed . Last year Drifter's was closed for remodeling and other places that would have live music might have a DJ. It probably will rain at some point during the day but we have been lucky not to have any hurricanes while there. We missed one by one week a couple years ago. We've been to YS falls a couple times and you will enjoy it. Been to the Pelican bar once. It seemed to be a long drive to get there and after about a hour I was ready to move on but had to wait for the boat to come pick us up.