The northern (and eastern) departure point near Virgin Gorda is preferable if you intend to island hop thru the Leewards and Windwards.
, which we took in 1993, is to go direct. It's about 415 nm if I remember right, and takes about 3-4 days. We departed thru the Norman Island-St John passage
angle at this time of year should be OK for close reaching, but its already hurricane
season and you'd want to watch the weather
closely because once you depart on a direct course there's no stopping place until you reach Grenada.