We sailed twice late August both times around 23-25th of the month. Both 3 nights, because it is so affordable.
2011, hurricane Irene passed by the Florida coast, we were at WDW before hand. We thought it may be cancelled but basically found out from these boards that almost 95% of the time they sail.
Well, first night rough seas, dinner not so good. We could not stop at Castaway Cay due to the damage and clean up that was going on. So, we dock at Nassau, no one got off because they were cleaning up. We then took a little ride out to sea, if I remember correctly and came back to Nassau the next day. We were planning to stay aboard so we did. Not the best cruise due to missing ️CC but still good.
Now in 2014, we sailed almost the same time and we booked Concierge because it was so affordable. The weather was perfect, no problems. We even got a Cabana. It was a terrific cruise. So, that one made up for 2011.
Like another person mentioned, hurricane season is June to November, so it's a toss up. Fingers crossed for you.
I am sure you will be fine. Travel insurance!
We are cruising this October out of NYC, I am concerned about the weather,storms etc. and I just booked Bermuda for late October 2018, nervous about that one too. But that's cruising off the east coast.