You really are trying to be like a salmon and fight it upstream. I suppose it can be done but you would either be making like a motor boat
the whole way or tacking so much you will wear out your boat
- - Aug to Sept is dead square in the hurricane
season with some significant storms usually starting up in the western Caribbean
early and Atlantic Tropical Wave and local low pressure areas making your journey anything but pleasant.
- - If coast hopping up Columbia
watch out for Rio Barranquilla as it is a historical hot spot for attacks on cruisers. Same for Santa Maria. No adverse reports beyond there all the way to Cabo de la Vela. Once past Punta Gallinas you have a clear shot to Los Monjes and on to Aruba