Pardon my thread drift for just a moment (I'm not looking to crew!), but just thought I'd pass on a couple important pieces of info for you, your boat/crew, and everyone reading this.
1) Please have a look at these two threads, where you'll find a wealth of info on both:
-- passage planning / Atlantic weather info / forecasts / etc...
-- vessel and crew prep / the important things that will get you all there in one piece / etc...
2) Except for mechanical or medical
reasons, there is no reason to divert to Bermuda on an Eastbound Atlantic passage
from the Caribbean
to Europe (or Azores), especially if leaving from the eastern Caribbean
You will of course sail a course with the winds / weather
that you have, and except for a weird weather pattern that may develop, there is no meteorological reason to head
to Bermuda (from the eastern Caribbean) if heading to Europe.
And, in actuality, this generally places you in a less favorable wind
/ weather environment
, again especially when leaving from the eastern Caribbean!
3) While leaving from the Caribbean
in early May is doable, when heading for Europe, this is typically a bit early.....but even then, this is usually only done when sailing a more southern route
And NOT when heading more northerly (especially when west of 50*W - 55*W)....as doing so will place you in direct path of Continental Lows (cold-core Lows) and their fronts, as they come off the coast of N. America....and while these Lows do move quickly, then also can pack a significant wallop!!
Despite the rally organizers' desire to promote their passage plan as "getting you to Europe in time to enjoy the whole summer sailing season", the fact is that this is typically WAY TOO EARLY to cross the Atlantic eastbound, especially if you're heading thru Bermuda (or even worse, leaving from the Chesapeake!)!
(of course it can be done, and it can be done safely....but it isn't the way to "plan" to do it safely and for fun....delivery skippers do it, racers do it, commercial
ships do it, etc....but a cruising boat
on a fun trip??? No, it is way too early...)
PLEASE read the details in the above referenced threads!
Fair winds to all.