Estonia and Finland have centuries of collaboration, mainly between the capital areas of Tallinn and Helsinki that currently account for 2 million inhabitants and USD 76 billion in economic output. The entry of Estonia into the European Union and, since the mid-2000s, a two-hour ferry trip, have both facilitated flows of people and merchandise across the Gulf of Finland. The different levels of development between Helsinki and Tallinn result in many asymmetric flows (workers to Helsinki, tourists to Tallinn). Beyond infrastructure and labour market issues, there are interesting opportunities for joint innovation policy efforts given their shared strengths such as in ICT, a dynamic start-up environment and technologically sophisticated public services. Cross-border collaboration can help build an “entrepreneurial knowledge region” brand. *