In the early 1980s, Sistren’s work became increasingly political through the group’s involvement in the Caribbean women’s movement, as was reflected in the topics of its plays and workshops. This chapter discusses Sistren’s transnational alliances in Jamaica, Belize, Guyana, Canada and the UK to assess the extent to which the group was able to map countertopographies (a concept developed by geographer Cindi Katz) through its popular theatre workshops. These workshops were conducted with women’s groups in the Caribbean region and internationally in order to forge political and economic alliances as a mode of resistance to globalisation and its effects. In this chapter, Sistren’s Women and Work project in which three workshop plays were developed: Domestick (1981/1982, three versions), The Case of Miss Iris Armstrong (1982) (two versions), Tribute to Gloria Who Overcame Death (1983) will be discussed.