I would encourage you to figure out where you are going as you do it. I have sailed in the BVI 3 times and never knew where I would end up when I woke up in the morning. I like to get underway pretty early and sometime after lunch think about what anchorages we are near. Last time we were there for 8 days and did 3 laps of Tortola but kept the route pretty different each time and spent some time in US waters. The distances are not that great and any anchorage is an easy days sail from any other unless you include Anegada.
The reason that they generally suggest a counterclockwise trip is that it is generally less rough. When you are sailing up the east side, it is more protected(unless you are outside of the islands) and you are on the wind, then you turn and run off before it down the west side.
Something to keep in mind about looking at anchorages is that the wind blows all night down there. The
anchors that the charter companies provide are shockingly small and it can be quite windy during certain times (they refer to the christmas winds for a reason). I much prefer to hang to a hook rather than be on a mooring but on the windy nights, I headed for a mooring so that I could sleep better.
Another cool place to explore besides the ones mentioned above is Norman's.
