The energy transition of Dutch shipping will be a complex gradual process due to the variety, cost and lifetime of vessels. The uncertainty in transition pathway, additional costs of climate neutral alternatives and required regulatory changes also form transition barriers. This thesis aims to create a holistic overview of both the transition barriers and the required enablers in which the focus will lay on pilot projects. These are carrierd out by launching customers and play a crucial role in the transition. Using the socio-technical multi-level perspective as a framework, literature on lock-in mechanisms, strategic niche management, transition pathways and shipping specific aspects was evaluated as a starting point for conducting semi-structured interviews with industry experts. These were used to study the transition barriers, enablers and pilot projects in depth. Three case studies were conducted for additional detail, context and reflection on the theory provided by experts. Pilot projects have the ability to remove any market entry barrier for a certain vessel and operational area. These barriers can originate from interdependency, uncertainty, the required assets, regulations and mindset. Pilots can also significantly reduce the additional costs of climate neutral sailing by tens of percent, creating opportunities for follow-ups, scale-ups and spin-offs. Furthermore, pilots can develop clear climate neutral sailing practices, the new ’ways of doing’, which articulates expectations and visions on a future climate neutral cluster which makes investments less risky.