As freshwater scarcity has become one of the most important environmental and social issues of the 21st century, the way the built environment interacts with water must be reconsidered. Today’s urban water cycle in Curaçao is characterized by linear, centralized, polluting, costly, time and energy consuming and does not contribute to cultural value. Architecture can play part in creating a more efficient and sustainable urban water system, while increasing the public awareness of issues related to the freshwater cycle. Heritage of water typologies and systems like water plantations, cisterns and wells give example of how Curaçao used decentralized micro water catchment systems (MWCS), in the pre-desalination period, to provide freshwater for the communities inhabiting it. In addition to the concept of these heritage inspired designs solutions (HIDS) the concept of current nature-based solutions (NBS), referring to ecosystem-based and biomimetic approaches, are analysed as alternatives. The integration of HIDS and NBS is a much-needed step forward towards an integrated and holistic approach of spatial planning and design in general and water related design and management in particular. ‘Regenerative Ruins’ focuses on the neighbourhood Otrobanda, centrally located in the capital Willemstad of the island Curaçao. The island has a rich history of urbanization in which the natural freshwater cycles have been neglected. As a result, the island is dependent to obtain its freshwater from a centralized desalination plant. The trend to live in the peri-urban area of Willemstad also led to an exodus of the formerly renowned labour district of Otrobanda, resulting in a cityscape dominated by decaying monuments. The project provides a solution to both problems by transforming a dilapidated monument into a regenerative decentralized freshwater production space, whereby the existing envelope becomes a central freshwater harvesting courtyard.