This is far from a unique trip or time of year. At most, its a couple of weeks before the southerly mass migration of the floating species. Most that I know, if they don't do the ICW, take one offshore passage to a mid-coast destination (VA, NC, SC) and then ride the coast the rest of the way. Pros or not.
Insurance usually keeps most north of NC until Nov 1, but not all.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.