We will be there around the same time on my brother's Sunsail 444 named Let's Play Two. Look for us, we will be flying the W!

Being a first timer I'm impressed with your itinerary. We are doing something very similar and have been going for years! Of course our world is a bit different than yours as our kids are now in their early 20's. We will have three 20 year olds and two 24 year olds. A different kind of crazy for sure!

In North Sound I would also suggest renting a car. Much cheaper, the roads aren't busy and you can see more of the island and go on your own time. Just keep saying "stay left" to yourself especially when making a turn. If no mooring balls at Leverick we either grab a mooring ball or anchor near Prickly Pear. We have always loved this little island although the last time we went they wanted you to pay for the use of the beach chairs even when we bought a drink. Not sure if the bar/restaurant is back up and running but pre-IrmaMaria they had the best Bushwackers in all of our taste tests (and we tasted many)!

We LOVE Cooper and would never miss it. Huge barracudas rest in the shade under your boat and the snorkeling off Cistern Point is pretty good and easy for kids. There is often a dolphin hanging out in the bay and my kids even got to swim with it one year. The last time we were there the dolphin "Peter" had a baby with her. The Rum Bar is always #1 on our list of spots to stop.

We have also hung out at Scrub Island and we loved it. We decided to dock that night and it was a great experience with the pool right there and it had amazing showers. I would definitely do this over Trellis.

Just FYI, you can take the dinghy over to White Bay from Great Harbor. You might get a little wet but it's cheaper than a taxi and we have seen dolphins on the trip over before. Just be careful to avoid the shallow parts of the reef on your way into White Bay. We have seen people hit the reef even in a dinghy.