Sailed this route (via the Azores) 2007.
Timing - end of May, beginning of June.
1) it is not good enough to 'believe' she goes upwind (in both heavy and light airs) - you need to know if she does or does not, otherwise take some fuel
, I say some but I mean a lot - you will re-fuell in the Azores
2) it can be done direct - beware the pilot charts
are statistics and they help you plan, but just do not stick to the plan - you will have to sail by whatever the weather in a particular year brings you,
3) if the High sits very, very S, then you will have to sail to the N of it,
4) but otherwise it is generally possible to start beating until the wind gets lighter, then tack below the High towards the Azores (actually S of the group) and then you catch up with the wind from the other half of the system and continue to Europe
(N. Spain or Gibraltar),
5) but if you aim for England
then you go N of the High pressure system,
We sailed a 26ft long keel
design 30 days from the Guadeloupe
to the Azores, on to Cascais (Portugal). All very easy except the first couple of days a bit on the windy side (beating into 20-25 knots of wind). Engine
used only to charge the batteries. In a !good! 45 footer if the winds are OK you will have no problem going, direct or not.