The first diaspora of Portuguese subjects originating from Macau (the Macanese) to various port cities in East Asia began in the 1840s with the British colonisation of Hong Kong. By the early twentieth century, their presence in Macau and resettlement in the Shanghai International Settlement, British Hong Kong, and Kobe led to complex diversification of the “Portuguese” identity. This study examines Macanese experiences in their navigation through notions of cosmopolitanism and patriotism in East Asian territories that were neither fatherland nor homeland. The debates show not only the vulnerability of Portuguese solidarity amongst the Macanese but also unprecedented ideas of being “Portuguese” in a relatively liberal British port city. Through the analysis of two national celebrations organised in British Hong Kong that caused tension, I explore how the shaping of cosmopolitan-minded Macanese in colonial port cities complicated notions of Portuguese patriotism, which oscillated between a love for the pátria (fatherland) and a sense of responsibility to fight for a progressive and just Macanese future. Their initiatives show that, away from the political centres of Portuguese power, the Macanese negotiated their relationship to the Portuguese Empire and competed for the authority to define “Portugueseness” across the East Asian littoral.