Wind direction is key for the Island, as you know, this time of year for any warmth. Keep the Westerly winds blowing & hold off the seabreeze as long as possible.
Already went through that this past weekend with the travel tournament kick off my son had. Made it to semi-finals before losing to the winner of the tournament but 4 games in two days with cold weather (40s) and rain was miserable. Sun will at least be out for your son's game.