Aside from running into some closures while you're down at that time, your itinerary sounds like a good one.

I think Cooper Island Beach Club will be closed at that time - as will Saba Rock in North Sound, I believe. Leverick will be open so if you have A/C, you might think about taking a slip there so you can hook up to shore power and save yourself using the generator - price is the same as a mooring ball -- electricity will be extra but you get ice and water fill-up included. I believe Soggy Dollar Bar will be open on JVD and I'm fairly sure Foxy's is as well. CGB will have places still open -- others can weigh in on closures.

Have a fantastic time and congratulations!