I don't know how well a 52' powercat goes to weather, it probably has sufficient power to push it; but once the waves and boat speed hit a certain value it might slam into rather than slice through the waves. But unless there is above-average waves and wind it won't make too much of a difference. The upwind leg on the north side of Tortola can be done in the open seas, or if waves pick up you can always slide in at Guana and through the channel past Leverick and be in somewhat protected waters.

If your charter starts at Norman then a clockwise route would have you head to Jost first, then Cane Garden Bay, then the North Sound, Anegada, and back to the Baths and Cooper/Norman.