All tourism destinations have unique characteristics that constitute their identity (Valls et al., 2012). Tourism companies, in turn, exploit these when planning and marketing product concepts for different market segments. In recent decades, the cities in the Baltic Sea region (BSR) have undergone a change considering their profiles as more well-known tourism destinations. Meanwhile, even the degree of professionalism in the tourism industry has increased. This opens opportunities for new forms of image marketing (Lucarelli & Berg, 2011). In order to understand city tourism better a comparison between urban and rural tourism will be made. Each destination and the associated companies have to develop their products and marketing campaigns in order to effectively promote themselves to various tourist segments. The purpose of this research project is to investigate the characteristics of city destinations, and how tourist segments translate them into destination images, and further how the image influences motivations for travel choice. Our theoretical framework consists of city destination concepts, destination characteristics and images, tourist segments' motivations and destination branding. In our pilot study, typical characteristics and tourist segments were found in the case of destination Stockholm. This result will be used when investigating how different tourist segments translate characteristics to an image perception. The planned research will take a multidisciplinary approach with an explorative purpose. A case study of two typical BSR-cities will be conducted, using interviews, statistical data, web site analysis and destination document studies. The knowledge contribution relates primarily to new forms of city destination characteristics and their impact on visitor travel motivators. Furthermore, a model for investigating segments' “image positions” will be developed based on a new kind of demand of city tourism and a more professional tourism industry, even though it is a complex task to determine image positions (Stepchenkova & Mills, 2010). Our hypothesis is that tourist segments are more interested in what city destination can offer today, but the supply side needs more knowledge how to influence the segments' travel motivators. We hope that the acquired knowledge will support destination organisations (DMO) and tourism companies to develop their tools for image marketing.