It all depends. October is in hurricane season, but that only means that chances are bigger there will be a hurricane or tropical storm than in, say, February. We sailed in late September this year, found the weather hot - remember the sea temp is in the upper 80's this time of year - and more humid than in our wintertime. Some rain, though most days were partly cloudy. There were 3 hurricanes spinning around in the Atlantic & Caribbean, but we missed all of them. Seas fairly calm during that time. Luck of the draw. Prices tend to be better in the fall due to hurricane season, however.
Remember - weather can never be guaranteed, no matter what time of year! If you don't mind heat & humidity, I'd say go for it!