Geo-political events, socio-economic conditions and technological advances have directly influenced the leisure cruise tourism sector. However, despite these challenges, cruising continues to experience exceptional growth, often re-inventing itself as a direct response. Projecting into the future, climate change, ongoing geo-political conflict and changes in technology are likely to produce the next epochs of reinvention of leisure cruising, as already being demonstrated. This chapter discusses the major milestones which define each of the broad challenges identified above and describes the cruise industry’s response to them.