This thesis examines the concept of sustainable touring for Singaporean musicians, exploring the challenges and opportunities that arise when touring internationally and regionally. While touring has always been a crucial aspect for building a full-time, sustainable career for musicians, rising costs and logistical challenges, especially in a post-pandemic world, have made touring more difficult for many artists. Nevertheless, successful examples of Singaporean musicians touring internationally and regionally prove that it is possible with significant time, effort, resources and connections. This research aims to map behavioural patterns of Singaporean musicians and their managers to find common factors and strategies that led to successful tours. The essay will focus on exploring the importance of touring, cultural differences within international audiences, the rationale for and logistical planning processes behind each tour, and sustainability for health and well-being on the road.