Piloting large vessels in increasingly congested waterways is no simple task. As in many ‘decision-making under uncertainty’ scenarios, masters, mates and pilots engaged in piloting are inundated with much information and required to make crucial decisions in real time. Piloting is also an inherently judgmental activity. Pilots and ships' captains invariably develop heuristics for transiting particular waterways. As vessels become larger, cargoes more hazardous, and the waterways more congested, decision aid technology is being considered to improve piloting decision-making. This paper describes one approach to providing improved on-board decision support to masters, mates on watch, and pilots navigating in restricted waters. We discuss (1) the use of cognitive decision aids in piloting, (2) the design of such a decision aid developed for New York harbour, (3) simulator experiments evaluating the expert system, and (4) plans to apply the approach and ‘lessons learned’ to the development of an expert system for tankers transiting the Gulf of Alaska.