Restricted water transits by U. S. Navy ships require detailed planning by Commanding Officers, Navigators and the entire ship control watch team. The methodical maritime navigation planning process currently used has not changed appreciably since World War Two. The process remains a manual one, relying primarily on hard copy data (which is distributed via the U. S. Postal system or other Governmental shipping means) for updates to the navigation picture. The explosion of information sources and technology provides an opportunity to revolutionize the entire maritime navigation planning process. The thesis contains an overview of the current manual navigation planning process used by the U.S. Navy. Alternatives for migrating the current method to an automated process are explored. A requirements analysis is conducted to capture fleet navigator feedback for a prototype automated navigation planning tool. Conclusions drawn from this study are implemented in the prototype on-line navigation planning tool that has been dubbed "GatorNet." Additionally, a requirements document is developed with the objective of shifting the maritime navigation planning and debriefing paradigm from a manual mindset to an automated one.