Hey, Jeff . . .
My wife and I have done this twice. The first time we took a guide and the three of us left from Gustavia and circled the island counterclockwise. Under stable weather conditions the trip had calm as we headed for Grand Fond, then super uncalm rounding that end of the island, then gradually more calm passing Flamands and then calm again passing by Colombier. I was glad we had a guide because the seas were mentally daunting in the higher waves and wind. And those conditions don't usually frighten me.
The second time was with our teenage boys and again we departed from Gustavia and just spent a couple hours playing around in the area between Saline and Shell Beach, which is quite beautiful from the water . . . The open cliff facings and the smooth waters in this zone made the experience an absolute winner. There was no need to do the full loop .. . too much stress and work.
I would go to Jicky or one of the others over in Gustavia and try to find a source here. Leaving from Grand Cul de Sac is just not the best zone for a pleasant experience.
Also, even though this was not your question, if you go into Colombier . . . . remember there are lots of bobbing turtles that are no match for speeding machines.
Hope this helps. Have fun.