The task of maritime pilots is to support safe navigation of ships, e.g. in port waters, and berthing in harbors. Contemporary ships tend to become continually larger due to economic needs. This trend makes the job of pilots more and more challenging. As a consequence the need for electronic support specifically tailored to pilots’ practical requirements grows. The paper will present a graphical user interface design based on Smart Glasses to support pilots in harbor maneuvers. In many harbors, pilots are already supported by Portable Pilot Units (PPUs) usually displaying navigational information on a tablet or laptop. These devices require pilots to look down and to move their gaze away from the most important information source, the direct ship environment. Smart Glasses would allow the pilot to continually look outside of the window and thereby keep focused on the relevant working context. The graphical design has been developed using the well-established Ecological Interface Design (EID) method . This approach has the aim to create interfaces which provide assistance to detect and solve problems especially in unforeseen situations. In accordance with the EID approach we performed a Work Domain Analysis and developed an abstraction hierarchy of the ship in its environment. Additionally, we conducted empirical studies to derive interface requirements in close cooperation with pilots from different harbors in Germany. The interface design takes into account the complete socio-technical system consisting of pilot, vessel, vessel crew, and supporting tugs and tug masters. A prototype has been developed on state-of-the-art Smart Glass devices. The design has finally been evaluated using a scenario-based interview technique. This evaluation underlined the promising opportunities of Smart Glasses for pilots and allowed to derive further requirements to tailor the design even more to the practical needs of pilots.