Navigational safety analysis relying on collision statistics is often hampered because of the low number of observations. A promising alternative approach that overcomes this problem is proposed in this paper. By analyzing critical vessel interactions this approach proactively measures collision risk in port waters. The proposed method is illustrated for quantitative measurement of collision risks in Singapore port fairways, and validated by examining correlations between the measured risks with those perceived by pilots. This method is an ethically appealing alternative to the collision-based analysis for fast, reliable and effective safety assessment, thus possessing great potential for managing collision risks in port waters.