This paper provides current results of a multi-year research project that involves the systematic investigation of ship air wakes using an instrumented United States Naval Academy (USNA) YP (Patrol Craft, Training). The objective is to validate and improveComputational Fluid Dynamics (CFD) tools that will be useful in determining ship air wake impact on naval rotary wing vehicles. This project is funded by the Office of Naval Research and includes extensive coordination with Naval Air Systems Command. Currently, ship launch and recovery wind limits and envelopes for helicopters are primarily determined through at-sea in situ flight testing that is expensive and frequently difficult to schedule and complete. The time consuming and potentially risky flight testing is required, in part, because computational tools are not mature enough to adequately predict air flow and wake data in the lee of a ship with a complex superstructure. The top-side configuration of USNA YPs is similar to that of a destroyer or cruiser, and their size (length of 108 ft and above waterline height of 24 ft) allows for collection of air wake data with a Reynolds number that is the same order of magnitude as that of modern naval warships, an important consideration in aerodynamic modeling. A dedicated YP has been modified to add a flight deck and hangar-like structure to produce an air wake similar to that from a modern destroyer. Three-axis acoustic anemometers have been installed at various locations, including a large vertical array on the ship's bow to measure atmospheric boundary layers. Repeated testing on the modified YP is being conducted in the Chesapeake Bay, which allows for the collection of data over a wide range of wind conditions. Additionally, a 4% scale model of the modified YP has been constructed and tested in the USNA recirculating wind tunnel. Comparison of YP in situ data with similar data from wind tunnel testing and CFD simulations shows reasonable agreement for a headwind condition and for relative winds 15° and 30° off the starboard bow. Analysis also indicates that CFD simulations require modeling the velocity profile in the atmospheric boundary layer to improve simulation accuracy. Finally, off-ship turbulence data collected using an instrumented 4.5 ft rotor diameter radio controlled helicopter show that the detected off-ship air wake is present where predicted by CFD simulations.