We cruised last year in mid October and it was wonderful. I was worried about hurricanes, etc. but things were fine and I loved the weather, prefering it to cruising in December. We had one slightly cloudy day on Grand Caymen, but nothing that impacted any of our plans. I found the water and air temps to be perfect-not too cool and not too hot. I would definitely cruise that time of year again. The only thing is, technically it is hurricane season so it's good to be open to possible changes in the ininerary if that were to happen.