Augmented reality head-up displays (AR HUD) can be seen as a promising advancement of conventional head-up displays in vehicles. Information can be displayed in a contact analogue way in the real world by projecting it onto the vehicle’s windshield. Two major challenges for concept developers are to reduce masking caused by augmented reality (AR) content and to create concepts that work with the limited field of view (FOV). To examine these two challenges, we designed two contact analogue navigation concepts. We compared them to each other in a field study with a prototype car that contained a complete AR HUD testing environment. The participants were experts in interaction design, AR, HUDs, design, and sales. The experiment showed that the application of Gestalt Principles for AR HUD concept design to reduce masking can be a promising approach. In addition, suggestions for further improvement of contact analogue navigation concepts were collected.