The crew planning problem in the airline industry presents a very computationally complex problem of high importance to the business. Airlines must schedule crew members to ensure that all flights are staffed while remaining in compliance with the business needs and regulatory requirements set by entities such as unions and FAA. With the magnitude of operation of the prominent players in the airline industry today, the crew staffing problem proves very large and has become heavily reliant on operations research solution methodologies. An area of opportunity that has not yet been extensively researched lies in the planning of crew vacation. This paper develops a model driven by the idea of system risk that constructs an optimal vacation grid for the time period of one year. The model generates a daily allocation that maximizes vacation offering while ensuring a given level of system reliability. The model is then implemented using data from US Airways and model improvements are provided for practical application in the airline industry based on the output.