Hong Kong has numerous outlying islands that are relatively underdeveloped due to isolation from the urban core and are dependent on ferries. Concurrently, the Hong Kong Government has expressed a desire for outlying islands to be places for urban expansion and has proposed building more bridges, tunnels, and reclaimed land. Development of these fixed links may transform the outlying island communities’ current ways of life. Ferry operators struggle to maintain efficient operation, fleet investments, improved services, and attract passengers while competing with fixed link transport modes. Urban ferry transport has been resurgent in parts of Europe, North America, and Australia, but not Hong Kong. This paper identifies a new typology of island communities according to connectivity based on available transport links. Using census and ferry statistics, the socioeconomic development of island communities is analysed. The transport problems faced by outlying islands are further conceptualised, and possible scenarios for socially sustainable island futures are proposed.