Singapore is one of the best managed cities in the world. Innovative institutional design and efficient public administration are some of the key reasons behind Singapore’s success. Singapore’s electronic road pricing system has been hailed as a textbook example of congestion pricing, and the Housing Development Board’s provision of public housing has made housing affordability less of a concern in Singapore than in other economies that have experienced asset value booms. To analyse the impact of Singapore’s urban form on commuters’ travel routes, this chapter compares Singapore with Taipei, which has a comparable population size, population density, and transportation system to Singapore, but a significantly larger grid area. It considers as cul-de-sacs other similar street patterns such as loop streets, where there are usually two access points, as long as the main feature is a central collector road, branching out into closed dead-end local streets. The chapter discusses the relationship between a city’s structure and its urban form.