The Nordic self-governing regions (the Faroe Islands, Greenland and the Åland Islands) pose a specific context for careers guidance policy and practice. Characterised by their island topographies, small populations and historically minoritised languages, these regions have in recent years gained greater autonomy over their domestic affairs. As a result steps have been taken towards developing domestic careers guidance policy and practice suitable for their own territories. In this chapter case studies of two of these regions will be presented – Greenland and the Faroes – in order to explore the specific challenges and opportunities facing these communities. With both regions historically subordinate to the Danish crown, these communities have a shared inheritance in terms of education, economic and careers policy, and they also face shared challenges in terms of their distinctive labour markets, language contexts and concerns with migration. However, as this chapter will show the specific manifestation of these challenges, and responses to these challenges has differed between the communities. The findings demonstrate how the communities of Greenland and the Faroe Islands are developing approaches to careers guidance policy and practice which draw from existing Nordic approaches, and benefit substantially from Nordic co-operation, but which also challenge and develop their Nordic and specifically Danish inheritances to create distinctive new models.