Flying Finn, I agree with little boats expressed concern about the time of year. And I fear (as I am sure you do) that there may be some work to do on the boat before departure (and I referring to maintenance
, and not merely provisioning).
I also suspect that you are looking for an island where there is an international airport
, rather than one that will require a shuttle flight. I would suggest that in June from Puerto La Cruz, you may wish to remain somewhat flexible. I would make the passage
permitting, continue on up the Grenadines past St. Vincent to St. Lucia. I would not be trying to make it any further north than that before my planned trans-at passage
The advantage is that you have remained fairly far south (albeit even Grenada
, below the traditional hurricane belt, got flattened by Ivan a few years ago). Still, it would leave a myriad of hurricane holes that would always be within reach should the forecast
get ugly. Your late arriving crewmember could then fly directly to St. Lucia, should things go as planned, or make a last minute switch to Grenada, if you are forced to retreat back to the south. In addition, there are numerous shuttles on Liat and other small carriers to St. Vincent and various of the Grenadines in between.
No matter what, you are likely going to be slogging to windward for much of the trip - and things can still get pretty boisterous, even in June.