Techniques are disclosed for systems and methods to provide sailing information to users of a mobile structure. A sailing user interface system includes a logic device in communication with a compass or orientation sensor, a wind sensor, and/or a speed sensor. Sensor signals provided by the various sensors are used to determine a heading and a wind direction for the mobile structure, which can be referenced to Magnet North. The wind direction and heading may be used to orient a sail chart rendered by the logic device. The sail chart graphically indicates the heading of the mobile structure relative to the wind direction and a performance contour for the mobile structure. The sail chart may be displayed to a user to refine manual operation of the mobile structure, and the information rendered in the sail chart may be used to autopilot the mobile structure.