I have done it both ways in a 40' mono and agree with the clockwise suggestion unless you have settled conditions on south side of St. John. It can be a very uncomfortable beat into the wind with significant waves.

RickG did a great job of summarizing the various beaches and bays. One update is that Vie recently closed her snackbar for good. She stopped making the garlic chicken a while back and has now closed it completely.

Remember that water is not available except at the fuel dock near the NPS dock in Cruz Bay so plan accordingly.

Dolphin Market in Cruz Bay is the closest full service market to the dingy dock and it's not a bad walk except the last block is all uphill.