Landscape architecture is built from place. What place is depends how one reads a site, which then determines what qualities are engaged with, and how they are engaged with, by design. Sydney Harbour is one of the most celebrated and distinctive harbours in the world. The qualities of the indigenous, pre-European landscape have been referred to regularly in the history of Australian landscape architecture as a source of inspiration for a truly Australian language of landscape design. A range of different models of such an Australian language have been proposed and tested on landscape design sites on Sydney Harbour, models that are in a discourse both with the specific landscape and with local landscape architecture theory and practice, particularly in relation to ideas of ‘appropriateness’ in Australian landscape architecture. This essay examines arguments from the 1970s that proposed a ‘palette’ approach to appropriateness, along with a key project from that period, Long Nose Point Park, that demonstrates this approach. The essay will then discuss three recent projects on the Harbour and demonstrate that these projects transcend the ‘palette’ approach by engaging with specific relationships on their sites (a ‘relationships’ approach) that are tied to the cultural occupation of Sydney Harbour. Along the way, the reader will be introduced to the key figures and history of landscape architecture in Australia, and to the geography of Sydney Harbour with its various ecologies and milieus.