Going on holiday is often associated with taking the car or plane. Even for short distances, and where alternative, sustainable transportation modes would be available, we frequently choose the more unsustainable options. Affordability, comfortability, and time savings led to an increase in transportation, which in turn, negatively contributed to greenhouse gas emissions. The reduction in those emissions can be achieved by choosing public transportation. However, since transportation choices are often made unconsciously and habitually, it is crucial to transform those unsustainable habits into more sustainable ones. Contextual changes can serve as a catalyst. This research investigates whether pre-COVID-19 and pre-inflation unsustainable travel habits can be broken through the perceived impact of COVID-19, financial hardship, and green consumption values, increasing the intention for sustainable transportation modes using a survey design. We found that the context change, as such, does not predict future intentions to travel sustainably, but existing green consumption values do. Building on the self-activation theory, the results show that habits and the perceived impact of COVID-19 and financial hardship activate a person’s green consumption values. Consumers’ green values mediate the relationship between unsustainable habits and the intentions to use sustainable transportation modes, combining the habit discontinuity and self-activation hypotheses.