There used to be a ferry from Spanish town to Anegada that was easy to do. We have also sailed but that was years ago and I forget the name of the charter. Are you looking to sail or power boat? Sailing is not for me, I get seasick easily.
You can still ferry; Monday, Wednesday, and Friday you can take the boat the leaves from Road Town in the morning.
When it's running, the Anegada Expresss boat from Trellis stops to pick up passengers in the Yacht Harbour. Currently running Thursday, Saturday, Sunday.