Any trip starting in the USVI with hopes of Anegada during December/January should take in the potential for North Swell and or the "Christmas Winds". If Anegada is important to anyone I would make all the distance possible North and upwind on the first day the weather makes that possible your your crew and boat. Even if that means a first full day first light departure for North Sound or even direct to Anegada. The rest of the trip should be a down hill, down wind sleigh ride. Each crew and each boat is different. Anegada is long way uphill when the breeze and sea are up. I have done North Sound to Red Hook and back more than once in the same day.