Depends on your policy
When I started going south, my policy had no restriction as to when I could go. Over the years it went to Cape Hatteras and a few years later Cape Charles (bottom of the Chesapeake). The last policy stipulated north of Cape Charles until November 1st. Some policies have no restriction. I thought the insurance companies were thinking of changing this as what happens is that you have all these boats clustered in the bottom of the Chesapeake waiting for Nov 1 and all you need is one late hurricane to take care of these.