The lives of seafarers may provide examples of transnational connections prior to the globally interconnected era in which ‘transnationalism’ has risen to prominence. In this article, I examine the long-distance connections of seafarers from Southeast Asia who settled in Liverpool, UK. Drawing on oral history/life story interviews with Malay pakcik-pakcik (elders) in Liverpool, I examine the ways in which connections with Southeast Asia have changed over the course of their lives. Much of this concerns political geography, which is often overlooked in the literature on transnationalism. During the period of Liverpool's pre-eminence as a seaport, irrespective of the depth or intensity of maritime linkages with Southeast Asia, connections did not involve the crossing of ‘national’ borders. Ironically, transnational connections are being forged in the post-maritime stages of the lives of pakcik-pakcik in Liverpool. I also show how Malay ‘transnationalization’ has resulted from expanded technological possibilities for long-distance travel and communications. Post-maritime transnationalization takes place in a ‘community’ clubhouse in Toxteth where the lives, emotional attachments and memories of pakcik-pakcik are intertwined with those of people with diverse connections to contemporary Malaysia and Singapore.