Recent high profile collisions involving naval vessels point to potential deficiencies in current training processes. The current work evaluates a training tool, the Target Angle Simulator (TAS) which aims to improve junior officer bridge skill sets. TAS provides the ability for students to practice skills in a simulated environment, providing hands on experience which could improve knowledge retention when compared to traditional, classroom-style instruction. The current work reports the results of two experiments demonstrating the value added of the new training tools. Experienced (Advanced Division Officer Course) and inexperienced (non-military) populations used the new target angle simulator to learn how to estimate angle-on-bow calls and identify vessel types in both day and nighttime conditions. A pre-test/post-test protocol resulted in significant improvement for the inexperienced population when they were allowed to practice with the target angle simulator. Improvement was not significant for the experienced group but feedback was extremely positive. The results suggest that the TAS is an effective tool which may be most effective for incoming Basic Division Officer Course students, who have some sailing experience but little prior experience making angle-on-bow calls.