This paper is a report on a project to develop a computer-based technique to optimize two dimensional sail design. Overall, we consider two distinct problems. The first problem deals with an unconstrained optimization of the lift. Then, to develop the second problem, we introduce an integrated form of Stratford's separation criterion as a limiting constraint. Throughout the work, we incorporate a vortex lattice analysis to determine the lift on the sail, and in each case, we use an optimization algorithm called VMCON. In the final chapters, we present the results for a series of test cases and describe the areas of future research and development.