We thought it was odd, too, since all of our research indicated that most people travel the island loop counter-clockwise. But, this was we were told told during the briefing and on a printed handout that was provided (if I can locate it, I'll send you a copy). However, I spoke to a couple Moorings' captains, who told me that this was fine, if the winds were coming straight down the channel, which they were.
When following the recommended clockwise route, we, too, left Little Harbor to Trellis, but I turned around to head to Sopers Hole. The winds may have have been fine for well-accomplished sailors, but were too heavy for me. The waves had to be around 7' feet, and the bow on the 32.2 kept on plowing and dipping into the oncoming waves.