In this paper, we consider the challenges associated with providing a mobile computing system that helps users enjoy a more flexible relationship between time and travel. Current travel plans, especially in Western cultures, are dominated by a strict notion of time. The need to conform to schedules leads to increased pressures for travellers and inefficiencies when these schedules cannot be met. We are interested in exploring the extent to which mobile computing can be used to help travellers relax these schedules and adopt a more opportunistic approach to travel -- potentially helping to reduce the environmental, financial and societal costs of modern travel.