Harbor Hopping Offshore - Beaufort NC to Pensacola FL

[RolfP]

I am moving my boat down the east coast around FL to Pensacola over the winter. I would like to do most, if not all, of the trip on the outside, reserving the ICW for bad weather or impossible off-shore conditions and passages. I am singlehanding but will be inviting crew for those parts of my trip off shore that will require more than 8-12 hours on my own.

I am asking where it is along this route that I cannot harbor hop - given that I want to sail off-shore for the most part, where will I need to be off-shore for a period of time that safety suggests crew. I sail a fairly well-founded Morgan 383.