Christmas markets, ice skating, walking through illuminated winter wonderlands or a refreshing breeze of the sea have always been important factors for people’s entertainment and sanity during wintertime. European winter tourism is an important key actor of the GDP of European Countries. Winter tourism as a growing segment of the tourism industry has expanded beyond its traditional link with alpine skiing to a wide variety of activities and experiences. What do people look for when they travel to a city like Vienna and a coastal resort like Opatija during wintertime? What are the pull and motivation factors that contribute to the choice of these destinations? What challenges and opportunities has winter tourism in the case of Vienna in Austria and Opatija in Croatia to offer - also in order towards a positive development for the future? These significant questions are the main basis for the topic of this thesis. The purpose of this paper is to compare and analyse the potential of two popular but different European tourism destinations considering their historical development of tourism and the current situation in each of these extraordinary places, and to consider how Vienna and Opatija are facing current (global economic and environmental) challenges to be a desirable winter tourist destination in the future. In facing recent challenges such as environmental concerns, technological developments, or socio-demographic changes this study will show opportunities and marketing strategies to make winter tourism even more attractive in both destinations. To fulfil the research purpose different destination images and marketing strategies from conventional materials (secondary data sources) are identified through the content analysis. The results indicate that there are significantly different motivations and pull factors in choosing Vienna and Opatija as winter destinations. Findings from this paper show that the historical significance of each are attractive criterion for both places. Health treatments, especially because of the Mediterranean Sea, the mild climate, the wonderful nature, and the many relaxation options were the most important motivation factors for staying in the coastal resort Opatija during wintertime. The great culture and (classical) music offerings as well as the many evening events are important factors for choosing the city of Vienna as a winter destination. Furthermore, future-orientated developments are required to fulfil the satisfaction of a stay in each of the two destinations.