It is all subjective, depends on many many factors, and all of those factors are basically personal decisions aided, abetted or disabled at the whims of weather , sea conditions and on time plane travel.

Easiest on you ? Heck, I could make it easy on myself and check out of JVD, check in at Cruz Bay, move to Christmas Cove for anywhere from part of a day to an overnight, motor back into Cruz to meet the ferry with my crew, motor up to Waterlemon Cay, set the hook, and treat myself and the crew to one of my favorite places in the VI's. Spend a night there and then check back in through JVD. That would be easy for me and I have huge doubts anyone else would complain about it. I'd have second thoughts about traversing Pillsbury Sound on the in and the out to Crown Bay or AYH, but that is just me and my subjective opinion.