For having a boat for only 5 days you might want to consider not going to Anegada. You will be limited on the number of places to visit stress free so you need to decide where you really want to go and factor in the time you want to spend at each place you go. Personally, I don't go to Anegada unless I can spend 2 days there. If I had 5 nights, I'd most likely spend night one at Marina Cay, next to nights at Anegada, next night in Great Harbor/Foxy's- Soggy Dollar and last night at Norman. Or do something like, Copper, North Sound, Cane Garden Bay, Great Harbor and Norman. Regardless where you go, you'll have a great time.
With the exception of our first BVI trip we have never missed Anegada so we would do a one day visit on a 5 day vacation BUT we have a powercat. If you are sailing I would trust the opinion of the sailors on this board.
After all these years, I am still amazed at how people think that Anegada is out of reach on a short trip. For Pete's sake, worst case it is less than 3 hours from the North Sound, and if the wind has any south in it, it is less than 2 hours. It takes longer than that to sail from Cooper Island to the North Sound!