I would not consider any later than the last week of July. After that things start to close up. You will not be alone then either. I expect some bargain charter prices about then. Might consider letting your son invite a friend (or two) along. Leverick, Pirates in the Bight, much of Great Harbor and White Bay and all of Anegada should be 75 to 80% back close to normal. Possibly even TOO recovered. It will take several years to recover the funky patina of the old beach bars.