When a sailboat is sailing in the general direction of the wind, it is known as downwind sailing. Under these conditions boats generally carry two sails - a mainsail and a spinnaker. The flow over these sails is complicated and poorly understood. An issue of importance to sailors is how the adjustment of one sail affects the aerodynamics of the other sail and the total driving force. In the present work a CFD analysis was performed on two different sailboat rigs, with an emphasis on the interactions between the main and spinnaker. The results show that the optimum angle of attack of the mainsail is generally 60° to 70°, depending on the direction of the wind relative to the boat. The correct setting for a mainsail has been a point of debate amongst sailors, and the present analysis supports the theory of easing the mainsail until it luffs (or flaps), then pulling it in. A surprising result is that when the wind is directly behind the boat, the mainsail should not be set to maximize projected area, but eased out past 90°. This is difficult to accomplish in practice due to restrictions of the rig, but raise some interesting questions.