Zanshin said:
I've seen many an excited BVI traveller make detailed sailing plans before the trip (as I've done in the past as well) who have been disappointed because they've stuck to the plan.
The major variable in all of these sailing plans is the weather. If the seas are flat and the winds regular then a counter clockwise sail going upwind on the weather side is perfect; but if the seas are up and then winds strong then attempting the same itinerary will be sporting or difficult. So plan both directions and decided once you get there.
(The other major factors disrupting carefully laid itineraries are, in no particular order: hangovers, seasickness, loving an anchorage, hating an anchorage, needing to replenish water and/or food and/or alcohol)