We are chartering this early July (leaving the docks on Sunday 7/3 from Road Town) and we are debating about which way do we go first-right towards The Bight, straight towards Cooper or left towards VG. We typically always go right but are tempted to make it to the North Sound earlier in the trip and do the backside of Tortola and JVD towards the end of the trip. How crowded does Cooper get on a Sunday with what I imagine many charters starting on a Sat or Sunday?

A lot depends upon the time of day you get to depart the charter base and what you can reach (or are willing to reach) before dark. The sea state plays a big role on the windward side of Tortola, if the seas and winds are up then counterclockwise is easier as the upwind legs are in the Sir Francis Drake rather than on the exposed northern side of Tortola...