It really does not matter. They are about 30 minutes apart. I would base it on your plans ashore based on what is open. You will also want to make a few day stops in the ares. For the first trip Sandy Isle and White Bay would be my choice. Leave Anegada early and plan lunch at Sandy Isle. Kids truly love that place. Motor 10 minutes over to Great harbor for the evening. The next day head over to White Bay for the lunch stop and then later in the day sail to CDB.