I think you are probably trying to fit in too much. Hitting the opposite ends of the BVI is certainly doable and if you are there to sail (not our primary focus) you'll spend a lot of time doing it. We prefer to spend more time at stops enjoying the water, snorkeling..etc.

I'd suggest doing as much as you can that first day - boat briefing, chart briefing..etc. Then see if its possible to have the skipper join you early the next morning. The earlier you get off, the better.

As Jbuch said its a decent trip up to the North Sound. You may be better off making a stop at the dogs that day. Then spend two nights at Leverick and explore the island. This would also have you at Leverick for the BBQ. Go to Coco Mayo or some place on island Thursday night.

Then on the 23rd, rather than sleeping in.. get an early start and you can get to JVD around the same time - break it up with a stop at Monkey point on the way. Then the rest could remain the same.