I'd consider making the first night away from the dock at Leverick to avoid spending most of the last full day on the boat sailing (or likely motor sailing) from Norman to North Sound. Also will make you first day less stressful since you won't be in such a hurry trying to get off the dock and to Anegada while you still have good light overhead. I guess that messes with your plans to be at the Friday BBQ, but Friday at the Willie T should be fun too.

We spent a night at Diamond Cay this last trip and it was nice. Main reason we were there is for kiteboarding at Sandy Spit, but we had fun in the Bubbly Pool and drinks at Foxys Taboo. Not very lively but a nice stop nonetheless.

We also chartered with Dream and I loved beginning and ending at Scrub. Especially ending there we were able to take nice showers and get cleaned up before the long trip home.

Have fun!