Terry,
Later in May is better than earlier. Less chance of running into foul WX.
The route from STT to the Bahamas or T&C is well-traveled. Here's how we did it in 2002:
Gallery :: Bahamas Trip 2002
Click twice on each pic/chart for full resolution.
Culebra is certainly nice and worth a visit, but you might wanna skip it this time. Not a great place to provision (as STT most certainly is), and only a few hours west of STT.
It would be good to have at least one crewmember aboard with offshore experience, IMHO.
Cheers,
Bill