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.