Decide at the outset that Jost, CGB, and Norman island are not where you want to be with your younger one. Get up to Leverick at least, decide soon and if you think you might want a slip or dockage at Leverick, make reservations. You can always change your mind, and those slips will be at a premium by Christmas. I second the idea of Anegada for Old Years Night. The Anagadian community is beyond skilled in helping you to have everything you need, and still making it fun. That, however, is a sail leg in the BVI that warrants real-time wind and sea-state forecasts that you can't have in your pocket right now. Leverick reservations to hold your place ( and the resort does do a great holiday spread), but that's also the easiest start point for the sail to Anegada.