1) I would avoid departure in late May,
2) time your departure well, as this is the only part of the voyage where you have 'control' over the weather
3) there are no magic tricks: you are sailing Westwards and the only tactical decision is how much (and if) Southing to make,
4) Personally, I would elect a wx-conservative route
, to avoid any risk from any early tropical disturbance/storm,
5) Personally, I would either receive radiofaxes or else use an external wx support (via a sat phone
or a two-way sat communicator), just in case.
Get yourself a good bimini
(for the sun, and for the rain), good shades, sunblock and something interesting to read.
better than autopilot
, unless you have a good autopilot
and plenty of juice.