Mobile multimachine work environments, in general, consist of varying types of machines driving across a site to complete a moving or manipulation task. As the view from the machines over the environment can be limited due to the structure of the machines, the environment, and the moved/manipulated items, there is a risk of collision between machines. In this paper, we propose a situation awareness system aimed as a driver/operator assistive system to enhance the safety and efficiency of multimachine work environments. The system consists of the pose estimation of the machines, the M2M communication based on IEEE 802.11p, the future pose prediction of the machines, and a graphical user interface. The system is designed to be general enough to be applicable in diverse work environments, which is most easily implemented as a retrofit for existing machines. In this paper, the implementation of the system presented is a proof of concept, and the focus is on how the overall system works in a real harbor environment during operation, ultimately aiming for the collision avoidance of harbor machines. The field tests show promising results, particularly regarding the applicability of the M2M communication technology in a very challenging and uncertain harbor environment.