The paper presents a description of the evaluation phase of the Evolutionary Sets of Safe Ship Trajectories method. In general, the Evolutionary Sets of Safe Ship Trajectories method combines some of the assumptions of game theory with evolutionary programming and finds an optimal set of cooperating trajectories of all ships involved in an encounter situation. While developing a new version of this method, the authors decided to use real maps instead of a simplified polygon modelling and also to focus on better handling of COLREGS. The upgrade to the method enforced redesigning the evaluation phase of the evolutionary process. The new evaluation is thoroughly described and it is shown how evaluation affects final solutions returned by the method.