Autonomous, electric, urban passenger ferries are set to become a new mobility mode. They will provide cities and urban planners with a new tool in their infrastructure toolbox and offer citizens a sustainable, flexible, and democratic means of transportation across previously inaccessible waterways. However, no existing regulation appears to fit, and an appropriate approach needs to be designed. In its simplest form—the shortcut across a river or canal—an autonomous passenger ferry closely resembles the operation of a traditional cable ferry. The major difference is that the autonomous ferry follows a “virtual cable” instead of a physical one, remaining untethered towards land. The operation as it pertains to passenger safety and navigation, however, remains largely the same. For increasingly complex journeys in more exposed waters, longer distances, and with more traffic and other obstacles, the operation will increasingly resemble that of a traditional manned ferry. Which different levels of autonomy and manning will we need from these urban ferries? How can regulations be designed that ensure passenger safety without compromising financial viability? And how to ensure the societal trustworthiness of this new mobility mode? This chapter sets out to explore these questions, providing input to a future regulatory regime.