A planning tool plans movement of a boring tool for an underground drilling operation. The planning tool includes one or more wheels for rolling on a surface of the ground along a path responsive to movement by an operator to characterize the surface contour and to generate guidance for the boring tool to reach a target position. Planning can additionally be based on waypoints. The planning tool can be rolled unidirectionally or bidirectionally to characterize the surface contour. Bidirectional movement cancels accelerometer fixed bias. Path stitching is used to plan around obstacles. The planning tool can facilitate tracker placement. The planning tool can collect noise information for frequency selection purposes. A described technique maximizes linear drilling in an underground plan. Compensation and/or warnings are provided for unsteady, fast and slow movement of the planning tool while measuring the surface contour.