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.