There is primary two routes - the northern non-stop or I-66 route
leaves anywhere from the northern Bahamas
to Norfolk and heads east staying about the tropical trade wind
belt until you get to about W66 longitude then turns south to the Virgins. Reportedly it can take from a week to two week to do the route. You can probably expect some nasty weather/waves at least once.
- - The other route is done in short jumps through the Bahamas
riding in front of the cold fronts that sweep off the southeast USA. Miami
to Nassau/Exumas/Mayaguana then cross to the Turks and Caicos
. From there south to cross the trades to the Dominican Republic
(normally Luperon but OceanWorld/Puerto Plata is an option). Then the next weather
window east along the D.R. north coast to either Samana or direct to Puerto Rico
. Finally short early morning day hops along the south coast of Puerto Rico
until you get to the Virgins.
- - Theoretically possible to do it in a month or two, but normally it takes 3 months all depending upon the nature of the various cold fronts and how much fun you are having in the various stopping places. This route can and usually involves some serious crashing and bashing to windward - motor
sailing. More details are available from previous posters in the CF search function.