<p>The United States Navy intends to dramatically increase its uncrewed aerial system (UAS) footprint in the future. However, there is limited data available that analyzes drone operator workload when operating in the unsteady air flow region behind the superstructure of naval vessels. The United States Naval Academy operates a fleet of 108 foot vessels for the training of future naval officers. One of these vessels has been modified to simulate a guided missile destroyer (with the addition of a flight deck and observation booth). This, combined with the USNA custom build research UAS, affords a unique opportunity to research drone integration onto a naval vessel. This paper documents two years worth of research into operating small UASs in and around naval vessels while they are underway. It analyzes standard and proposed approach paths on during different headwind conditions using traditional flight test techniques. While our available data did not contain enough data points to reach a statistically significant threshold, we did not see a major difference between the three approach paths. However, this research proposes a possible method to aid test conductors in risk reduction during flight test of these highly automated vehicles.</p>