I need to re-write that post, the more I think about it, clockwise is the better route to take if doing a loop from Puerto del Rey or USVI. I shouldn't have let the base manager talk me into counter-clockwise.

Coming around the south side of Vieques was pretty rough with 10-15 knots right in our teeth from the east. Plus you are also fighting the prevailing current. Going clockwise, the eastward passage will have better protection from the swell in the lee of Culebra. Culebra to Vieques should be on a beam, and coming around Vieques, downwind.

Not sure if anyone else has any other thoughts. I've only done SVI once, but will make it two after our November trip.