Were it me (weather permitting of course), I would run outside to the mouth of the Chesapeake, then go inside and down through NC, coming back outside at the Beaufort Inlet. From there, a two night trip to Charleston, or north end of Hilton Head if you're making good time.
Say Charleston though, and a day trip, outside to North end of Hilton Head. From there you can do overnight hops outside to St Augustine, then Fort Pierce, then Miami (I would go past Government Cut and come in at Cape Florida).
That's my usual route, weather permitting. Southport NC to Georgetown SC gives you the most beautiful and ugliest stretches of the ICW (Waccama River and Myrtle Beach).
Say Charleston though, and a day trip, outside to North end of Hilton Head. From there you can do overnight hops outside to St Augustine, then Fort Pierce, then Miami (I would go past Government Cut and come in at Cape Florida).
That's my usual route, weather permitting. Southport NC to Georgetown SC gives you the most beautiful and ugliest stretches of the ICW (Waccama River and Myrtle Beach).