A series of four experiments were performed during an iterative design evolution of the human-computer interface (HCI) to a small unmanned surface vehicle (USV). The baseline control system was compared to several alternate designs using a simulated naval mission. User tasks included the monitoring and control of one or two vessels simultaneously. Faults and hazards were included to stimulate emergency responses during vessel transit. Alternate HCI designs varied across these factors: visual integration, synthetic audio feedback, sizing and placement of alerts, and use of a hand-held game controller as a primary input device. Results for N=32 sailors across the four studies indicated that for single or dual USV control conditions, the interface features added to the baseline design significantly improved speed and accuracy across multiple mission tasks. However, all design configurations still yielded some collision errors indicating that operator visual monitoring and manual control may be inadequate in complex, cluttered transit environments. Therefore, on-board automatic obstacle avoidance systems may be needed to safely support multiple vessel operations in cluttered complex transit environments.