During the late nineteenth century, Italian immigrant settlement in Wales took the form of chain and clustered migration, based on origin-centred networks of extended family members. The original migrants’ reliance on transnational family support networks endured and evolved through descendant generations. Family formation and the progression of lifecycle care exchanges served as key drivers of transnationalism between Wales and Italy. Many families established catering businesses in Wales that relied on staff recruitment from kin in Italy. Migrants’ heritage and affective anchorage to Italy were maintained through ‘circular’ mobility premised on endogamy and shared language. In recent decades, despite a decline in endogamous marriage, transnational family interaction has continued on the basis of the ease of European Union cross-border mobility. Changing modes and motives for cyclical and return migration encompass new forms of marriage, professional and retirement migration. Based on etnographic research with three generations of Italian migrants in Wales, this article explores the relation between family social networks and local attachment in supporting transnational practices, positive integration and heritage maintainance, tracing the cultural and social change in the generational process of migration.