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From mid-19th century onwards, the world was increasingly connected by modern modes of transportation and technologies of communication, such as railways, steamships, modern banking systems, the telegraph, and so on. In East and Southeast Asia, the highest degrees of connectivity were found in and between the capitals or maritime port cities, including Tokyo, Yokohama, Kobe, Nagasaki, Shanghai, Canton, Hong Kong, Manila, Saigon, Bangkok, Singapore, Batavia, and Rangoon. These cities were linked by steamship, rail, and telegraph services, and covered with networks extending the flows of people, commodities, money, and information. That era of deepening regional connectivity and flows in East and Southeast Asia corresponded with the peak of political revolutionary movements grounded in nationalism, communism, religion, or anti-colonialism. Colonial and national governments regarded these movements as threats, and closely monitored and severely suppressed political activists. Under such circumstances, many revolutionaries were forced into exile by arrest and deportation or in order to escape detention. Exiled activists regularly moved between different cities connected by modern transportation and communication technologies. The cities served as their bases from which they partook of many itineraries of revolutionary activity abroad. This paper focuses on the itineraries of three famous Asian revolutionaries, namely, Sun Yat-sen, Nguyen Ai Quoc, and Tan Malaka, who lived in exile from 1895 to 1916, from 1911 to 1941, and from 1922 to 1942 respectively. The paper offers a comparative study of the particular cities in which these exiled revolutionaries based or pursued their political movements, and explains why these cities were chosen for their arenas of revolutionary activity. Between them, the exiles lived and operated in Tokyo/Yokohama, Shanghai, Manila, Amoy, Canton, Hong Kong, Hanoi, Bangkok, Singapore, and Penang. These were the major maritime cities of Asia, serving as national or colonial state capitals or the leading trading centers in the region. Besides the advantage of having regular services of steamships and communication technologies at hand, the revolutionaries had differing reasons for selecting cities for their revolutionary headquarters. For example, Sun Yat-sen frequently visited and stayed in Tokyo/Yokohama because of his links with Japanese politicians, entrepreneurs, and supporters. On the other hand, Shanghai was the preferred city of underground revolutionaries, such as Tan Malaka, because Shanghai was divided into three municipalities. In short, a close understanding of the relations between cities and revolutionary movements requires a careful analysis of the political, economic, social, and historical background and character of the cities themselves.