This study focuses on local ice-breaking tourism initiatives in Kemi (Finland), Mombetsu (Japan), and Abashiri (Japan). It adds to research on winter and cruise tourism and analyzes multiscalar challenges—ranging from the global warming and COVID-19 pandemic to dependency on local governmental support—threatening the future of tourism dependent on frozen maritime conditions and vulnerable to changing climate conditions. As the case study cities have invested significantly in tourism built around the uncontrollable natural phenomenon, changes in this industry can lead to substantial spillover effects in the surrounding communities. This qualitative comparative research is based on extensive fieldwork and utilizes the concept of resilience to discuss the means of responding to existing and predicted disturbances. The results of this study show that the recent adaptation and resiliency-building strategies have focused on searching for alternative use of old, new, and renovated ice-breaking vessels, attraction of new types of (often domestic) visitors, and development of activities and facilities that are less sensitive to seasonal variation and climate change. While introducing new local ideas concerning ecological and educational tourism, e-tourism, and community-oriented tourism, this article contributes to the understanding of resilience-building processes in tourism.