The territorial autonomies in the world have developed in different constitutional and political environments, but there are also several similarities when it comes to the institutional aspects of how the territorial autonomies function and act in their relationship towards their respective metropolitan states. This paper will elucidate some of the island autonomies in a Nordic and a Portuguese context. The Nordic cousins are very much alike regarding the institutional design and in relationship with their respective metropolitan state, but their historical and political development have been of different character. The Portuguese islands of the Azores and Madeira have developed through another context. What are the similarities and differences between these islands?