It's a personal choice how you enjoy spending your time. I am assuming that you have a large charter boat so you travel faster than a small boat.

It will be a long day to north sound. Perhaps lots of motor sailing too. There are lots of moorings in north south plus anchoring opportunities. Anegada is not far from north sound. You should not have a problem arriving early enough for a mooring ball. The wonky dog is a great spot for dinner. Anegada to jvd is a nice sail. Easily doable with a lunch stop along the way. Lots of moorings in various places should be available,especially little harbour.

So, other than to long day to north sound, it sounds doable. However, why not shorten that day a little and with an early start the next day get into north sound in the following morning.