Moving a wheelchair is a task which requires both the physical and mental engagement of either an assistant pushing it, or the rider controlling it. Pushing it can be physically demanding and limits the number of wheelchairs that can be moved, to one. Our research introduces a technology that may enable a wheelchair to independently follow the rider or assistant. This will allow the rider to disengage from the task of moving the wheelchair, and allow for more riders to be assisted by an assistant at one time. We have developed a Socially Interactive, Gesture-Aware, Human-Following, Transport system (SIGHT) in order to provide more freedom of action to assistants who are providing the same level of service to riders with less effort. Indeed, SIGHT allows for a human to interact with the wheelchair on a more social level. By using gestures, such as waving, the assistant and wheelchair can communicate.