Culture and creativity represent an almost ubiquitous component of the international action of cities. A core feature—and a driver—of bilateral ties such as twinning or cooperation agreements, culture and creativity are frequently integrated into the economic strategies aimed at supporting local economic growth and job market. Additionally, over the last decade, cities have been implementing cultural and creative policies to foster social cohesion, promote diversity, and welcome migrants. City networks such as the Organization of World Heritage Cities, the World Cities Culture Forum, and the UNESCO Creative Cities Network act as both representatives of such approaches and as peer learning and advocacy platforms. The chapter will offer an insight into the tools and practices of cultural city diplomacy, taking into consideration both opportunities and challenges. Finally, the chapter will consider the impact of COVID-19 on such a component of city diplomacy.