Opinions are like itineraries- everybody has at least one smile

Me personally, I'd plan for going the other way- heading out of RT for a relatively short downwind(ish) sail to Norman for early arrival and chill first day, then work back east to Cooper, then North Sound, THEN downwind along North Coast to Jost. With random stops along the way. Done it both ways, and the counter clockwise is the one I remember as being best. Of course this is weather dependent. Anyway, now we don't really have an order- we just go. We just got back from our 5th charter a week ago (which still makes me a newbie too) and it was just great. Gets better every time. Have a great time.