Marc makes a good point about the northers that are not uncommon, usually about three days duration, during this time and on into the
winter, but there should be no difficulty in choosing to wait out these
events just as avoiding a late tropical storm. If you're taking coastal hops, the longest leg would be an overnight across Florida's "Big Bend" from areas near Appalachicola to Anclote Key or a shorter choice from St. Marks to Cedar Key. Your selections in this area depend on your
draft. Once to Tarpon Springs (Anclote Key) you are back to easy half day choices
offshore or the
ICW. 'many beautiful stops if you're not rushed.