This study compares Melaka and Penang in the context of overall trends - policy, geographical position, nature and direction of trade, and morphology and sociology - and how these factors were influenced by trade and policies. Conclusions are drawn concerning where and how Melaka and Penang fit in the urban traditions of Southeast Asia and the significance of the fact that the period under study coincided with the shift from the height of the "Age of Commerce" towards a period of heightened imperialist activities.