We cruised in late Oct. last year & I LOVED it. I don't like the hot, humid weather in Florida & the Bahamas in June (when we sailed before), and all of that was gone!!
I guess you will always run the risk of the hurricane season storm, but the odds rreally are in your favor. I would love to go in late oct. again -- the only problem we had was taking DS out of school. He missed a lot of activities & never really did get much homework done on board. So this time we're going again in June again... yukky weather, but better than no cruise at all of course!