While academic research and policy reports emphasize the new political assertiveness of urban centers as sub-national units, case studies have mostly concentrated on the world’s biggest cities, often forgetting smaller cities—that is the immense majority of the world’s urban centers. Available research has also had a distinct presentist feel, failing for the most part to consider current developments as emerging from past trends. This chapter studies the international outreach efforts of the city of Turku, located in Southwestern Finland. Finnish cities have been no exceptions in the recent development of city diplomacy, as they too have developed institutions and processes by which they have pursued internationally their political, cultural, and economic interests. These institutions and processes, though, have been the continuation of previous trends. Turku is a fantastic testing ground for that idea, as it has evolved from being Leningrad’s first twin city in the late 1960s to being a member of variouspol international organizations and EU-based Baltic cooperation schemes. The chapter further looks at the implication of Melissen and van der Pluijm’s (van der Pluijm & Melissen 2007) taxonomy of cities’ semi-diplomatic tasks (economic and commercial promotion, cultural and scientific relations, city branding, networking, information gathering, and lobbying).