It is a challenge of planning, it is a triumph of planning. It is a place with limited resources, it is a place with unleashed opportunities. This is a narrative of three tales of one city, the regional planning of Singapore. Singapore is a city-state known for its small size, dense population, economic success, and livable built environment. It is often related with ideologies such as efficiency, growth, technocracy, meritocracy, and sustainability. Prudent planning is what makes Singapore work, and its planning is laid out collectively across multiple statutory boards, involving different topics such as public housing, transit, and parks. Intrigued by its planning challenges and success, we examine the outcome of Singapore’s regional planning through three lenses: accommodation, accessibility, and nighttime activities, which are quantitatively evaluated by population density, transit centrality, and VENU Index. The comparison part weaves together the three branches, where we define new groups based on the distribution pattern of the 3 resources.