The advent of mechanisms for facilitating electronic commerce has triggered widespread interest in several fields. However, research in electronic commerce to include Smart Card Technology has mainly focused on land-based transactions. This research investigates the role of Information Technology in facilitating electronic commerce at sea, aboard U.S. Navy ships. It determines the feasibility of replacing the current cash shipboard architecture with a cashless network providing real time accounting and banking applications. This research verifies the feasibility of cashless network systems aboard ships with cashless mechanisms. The motivation for this research is to provide and ensure monetary freedom to sailors at sea. This research evaluates the efficiency of cash processes using Commercial off the Shelf technologies. It also identifies workload demands through automated networks, and verifies seamless integration with cashless processes available commercially. A review is conducted of the existing shipboard cash systems. Then, the motivation for electronic commerce on ships is discussed. Two active prototype solutions are investigated. And finally, some of the lessons learned based on the experiences of these prototypes are summarized with a recommendation for the future.