The paper presents a 3-stage synthesis-based Decision Support System for watchkeeping deck officers. Its functional scope covers conflict detection, maneuver selection, and maneuver execution, all phases supplemented by collision alerts. First, a customized elliptic ship domain is used for checking if both OS and TS will have enough free space. A survey-based navigators’ declarative OS arena is then used to determine the time at which OOW would like to take evasive action. Next, a safety level is assigned to the current situation based on the predicted violations of the ship domain and the declarative arena. The safety levels are also attributed to potential evasive maneuvers (single actions combining course alteration and rudder deflection). For a selected maneuver, Collision Avoidance Dynamic Critical Area (CADCA) is displayed, which informs OOW about the time window when the maneuver remains feasible. All of the above contribute to a holistic system of multi-level safety assessment utilizing: empirical ship domain, survey-based declarative arena, and ship dynamics-based CADCA. These, in turn, take into account navigators’ knowledge and preferences, ship maneuverability, and the impact of environmental conditions. The system is presented in three real-life scenarios located in the southern part of the Baltic Sea around the Danish straits.