Pilots are an important asset in the operations of airlines, as with insufficient pilots, an airline cannot operate the planned schedule. The long-term crew planning problem aims to optimally plan the supply and demand for pilots as well as methods and strategies for closing the gap between these. The demand is determined by the number of pilots required at each crew position based on the demand for the flight schedule, training requirements, contractual agreements for holidays and off-days. The supply, on the other hand, is determined by the current pilot workforce and changes over time by factors such as retirements and illness. Finally, the inevitable gap between supply and demand can be closed by planning transitions for pilots to different crew positions and by recruiting new pilots. This project addresses the cockpit crew transition planning problem. This is an optimisation problem that aims to optimally assign transitions for pilots with the goal to minimise the shortages and surpluses in the supply of pilots, constraint to for example contractual and governmental agreements and capacity limitations. A heuristic local search method has been developed to plan and evaluate transitions for pilots between different crew positions. A tree search method is then used to select, at each iteration, the transition with the highest potential. In an experiment on various configurations of the model, the results are compared and recommendations are made on the best method to model the cockpit crew transition planning problem.