Contemporary urban development places a critical emphasis on pedestrian environments, especially in historic cities like George Town, which is a UNESCO World Heritage Site in Malaysia. Although survey questionnaires effectively captured public perceptions of issues such as poor road connectivity, weak accessibility, crime and safety concerns in George Town, they fell short in providing a comprehensive understanding of the root causes. This study leverages space syntax theory to model and analyze George Town’s unique pedestrian landscape, aiming to identify strategies for improving pedestrian networks in historical urban landscapes. Space syntax theory, known for revealing structural issues within urban contexts, is applied after a thorough examination of George Town’s urban layout, climate, architectural features, and development policies. George Town employs an informal grid layout widely utilized in British colonial port cities to enhance overall efficiency. The predominant architectural form is the shophouse, which is characterized by a ground level designed for pedestrian movement known as the “five-foot way” and adapted to Malaysia’s climate. Various axis drawing methods for the unique five-foot way under different circumstances are considered. The George Town special area plan (SAP) emphasizing heritage preservation guides development policies, thus requiring an inclusive approach to pedestrian environments. This enhances the practical significance of the current study, with the eastern and northern coastal areas serving as crucial focal points for investigation. This approach results in a comprehensive spatial model that captures the essence of George Town’s pedestrian landscape. Evaluation using space syntax indicators such as connectivity, integration, intelligibility, and choice reveals issues like poor overall network connectivity, inadequate access to key attractions, suboptimal integration, concentrated pedestrian flows, and significant safety concerns, which are exacerbated by limited infrastructure on certain two-way roads and a lack of zebra crossings. The practical implications of this study include recommendations for enhancing pedestrian spaces along identified roads and strategically installing zebra-crossings. This research is significant for its focus on a historical city in a Southeast Asian developing country, deeply integrating local environmental characteristics and providing insights into urban planning and optimization, thereby serving as a reference for similar cities.