Re: The Thinking Man's Guide to Voyages South
I personally like to leave from Hilton Head and do not mind rounding Cape Hatteras. I rest up in Hilton Head and wait for the right time to leave. The CHART in the guide refers to leaving from Morehead as you surmised and as most sailors prefer as it is north of Cape Hatteras.
Whether you leave from Morehead or Hilton Head, the two challenges are to cross the Gulf Stream
and to pick up the trades.
I agree with Jimmy Cornell in "World Cruising Routes" Fifth edition, on page 176 where he says "One should proceed for at least
100 miles ESE direction so as to cross the Gulf Stream
at right angles"
Once you reach that position offshore, you will cross the Gulf Stream and that should put you almost due north of San Salvador which will be at that point about 560 miles to your south.
I do not believe you will be "upwind of the Windward passage" at that point as the Trade Winds will be E or north of E and you should be able to reach all the way down on a SSE heading to the Windward Passage.
I could have made this clearer in the book and will do so in the next edition.
From what you say about your limited offshore experience, I recommend you consider the Windward Passage as it allows for less offshore time and when you come to the Caribbean you will be on the Caribbean side of the islands and not on a lee coast.
I appreciate your interest and look forward to hearing from you again.
Also, 100 miles SE of Hilton Head is roughly longitude 79 degrees W (is that even past the stream?), and if you head south from there you'll be west of the Bahamas, not east, and still a good (upwind) distance from the Windward Passage.
The map that's on the guide shows this route starting from Morehead City, NC. And this one makes more sense with the context of your description of the route.
Is there something I'm misunderstanding or misreading?