Thanks for all the suggestions everyone. This is great information!

We are leaning against Anegada. We have enough time but this is our first trip and there is so much to do and see without going there. Don't get me wrong, I'd like to do it for the adventure of the sail alone, but the idea makes my wife nervous, and sometimes you just got to know when to push the family hard and when it's better to just chill out when everyone is already in a happy place. So we'll likely leave it for next time! (not promising I won't change my mind on this lol).

But here's another idea I'd like to get feedback on. We head out for Norman on our first day (the check out sail day) on a Friday. Cooper is on our list, so logically it's the next stop, which would put us there on a Saturday night. Which is the same night all the usual weekend charter starters and charter enders will be there, and it is already by all accounts the hardest mooring ball to get by either BoatyBall or FCFS. So I started thinking of a doing a clock-wise route to get offset from the rest of the weekend-start crowd. Then I thought better of it - conventional wisdom is what it is for a reason, even in summer, so a first-timer especially should heed it.

Then I got another idea. What about going directly from Norman to JVD and spending 2-3 days there and CGB (so just the downwind first leg of the clockwise route), and then backtrack sail to Cooper on Monday or Tuesday when it is less crowded (which is a finish leg on typical routes)? And from there on to Marina Cay, North Sound, etc. I think our kids might like the Jumbies beach BBQ on Friday night, and this is the only way we could do that, but that hardly seems like an event to plan your entire itinerary around. But I do like the idea of being a bit less with-the-crowd. Am I overthinking this for June, when it's not as crowded anyway?