Our last two Dream cruises were in late September and both were affected by hurricanes, Joachim in 2015 and Matthew last year. No big deal to me or my husband but the rough seas did get my daughter a bit. We were unable to go to Nassau, which was fine. We stayed right along the Florida coast to avoid the storm. CC was really windy and we docked late but we got to go. If anything, it made the cruise more exciting lol. Last year we watched from our veranda as they stripped the beach at CC in anticipation of Matthew coming. The cruise after ours was more affected, with an extra day at sea while they waited to see what would happen to Port Canaveral. I would't hesitate to cruise again in September or October but agree you need travel insurance.