I can tell you from personal experience that being seasick while trapped on a boat for a long time is absolutely awful. It's a great curse of my life that I love being out on the water, but am susceptible to seasickness.

I've never been seasick on our bareboat charters. Part of the reason is that we're in control:
  • Too rough motoring straight into the waves? Bear off at 45 degrees for an easier motion.
  • Big swells coming from the north? Head into the shadow of Great Dog Island for some relief.
  • Had enough for the day? Change destinations.

On the other hand, I have been seasick on the ferry from St. Thomas. Never while out in the open air, only when below deck. But at least it's all over in an hour or so.

So you might be ok going to Anegada -- she could have a lousy ride, but then recover and have a fun time. A day of island hopping, however, where you're committed to being on the boat for an extended time, could be risky unless there's an exit strategy.

And yes, I agree that the worst motion on a boat is when you're rocking on the waves and not under way, so that may be something you want to completely avoid.

Good luck!

Dan cheers