We left Annapolis September 8, 2001, sailed through Norfolk Sept 10 and left the Alligator River Marina Sept 11. A bit disconcerting sailing with fighter jets soaring overhead.
From there we went to New Bern, NC, left the boat until mid-October, returned for another 10 day cruise partially offshore
to Canaveral. Left the boat and returned mid-November to sail around the Keys and up to Charlotte Harbor/Punta Gorda -- came in Boca Grande Pass.
A bit south of where you want to end up, but we did a similar trip starting about the same time of year. We were lucky with no tropical storms, but there are lots of places to hole up and prep for a hurricane if necessary.