Abstract This article examines the life histories of three women who migrated from the island of Tobago in the period 1950 to 1990. The themes explored include the factors which motivated their move, their lived realities in ‘new’ lands, the impact of migration on them and their families, and the reasons for return migration. This article argues that from the first half of the twentieth century, working-class Tobago women, through their personal migration efforts, made use of ingenuity, psychological strength and ambition to better themselves and their families. The Caribbean labour migration literature highlights the migration treks of Caribbean men during this period, but Caribbean women travelled in equally large numbers regionally and internationally in a relentless pursuit of wage labour and economic stability. While in some instances, their migration experiences led to the achievement of promised upward mobility, the pain of deteriorating family relations and rejection in a ‘new’ land, often led to return migration. This argument, which rests upon an interrogation of life histories, newspapers and official documents, presents new insights on a familiar topic, and meaningfully expands the historiography of migration and Caribbean women.