Your boat and it's windward ability might influence your route
We did the passage
twice. Once with a Swan 42 and the following year with a Farr 38. We sailed in the days way before receiving weather
forecasts on board.
With the Swan we sailed St Helena, Assencion and then curved North, North west and then East around the Azores
high to Horta in the Azores
is then a short hop away. We very much followed the route as prescribed by Ocean Passages of the World.
The trick after leaving Assention is to keep the wind
just forward of the starboard beam and bend around the high. Eventualy the wind
moves aft and you then run and reach in to the Azores.
The next year we sailed the Farr 38 up. After Assencion we saild straight up to the Cape Verdes, mostly hard on the wind. Then straight up to Madeira
hard on the wind. Then to Gibraltar
, hard on the wind.
I suggest you sail via the Azores!
The joke is that somebody asked me the same question after I got home from the trip via Cape Verdes and Madeira
. It was at the Club and the guy was smashed. He got my answer all screwed up and went via Cape Verdes and Madeira..................and had following winds all the way! He returned home and thanked me for my good advice!
Serious though, I would go via the Azores. Horta is just simply a "must call" for ocean voyagers. It is an amazing ocean cross road.
Time to go? Depart from Cape Town
end- April, early May. That gives you good sailing up the South Atlantic before it gets too cold and you get to the Azores mid summer.