This paper presents the outcome of a pre-project that resulted in an initial version (prototype) of an automated assessment algorithm for a specific maritime operation. The prototype is based on identified control requirements that human operators must meet to conduct safe navigation. Current assessment methods of navigation in simulators involve subject matter experts, whose evaluations unfortunately have some limitations related to reproducibility and consistency. Automated assessment algorithms may address these limitations. For a prototype, our algorithm had a large correlation with evaluations performed by subject matter experts in assessment of navigation routes. The results indicate that further research in automated assessment of maritime navigation has merit. The algorithm can be a stepping stone in developing a consistent, unbiased, and transparent assessment module for evaluating maritime navigation performance.