It is not the beginning of May. It is May. And in Sept you may want to be already out.
Mind when departing from the Caribbean
side end of May you are around the Azores
in mid till late June. It is not a weekend trip. Plan your departures and arrivals accordingly.
Part of the problem is reading some books
without realizing where their author took his advice from. Then it is about remembering that routes and timings that applied to HMS tall ships may be less adequate for boats that are like 1/100 of the displacement
and 1/10 of the LOA
But whoever wants to know, will know. The info is out there. It is just that some of us elect not to do their homework.
Bigger boats, doing work (often half a year in the Med and the other half in the West Indies) are another story too - bigger, with young, strong, professional crews - they can. I know some skippers who if not for being on a job, would not.
When the boat is designed for less dramatic sea conditions one may be well advised and depart so that the crossing falls on the (statistically) easiest part of the season. Not that we will not get hit, only that our risks will be limited to the lowest level available.