The energy transition of Dutch shipping is a complex gradual process due to the variety in vessels, cost and lifetime of assets, uncertainty, additional costs of climate-neutral alternatives and required regulatory changes. This paper aims to create a holistic overview of both the transition barriers and enablers. A focus is placed on the significance of pilot projects. 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 determining the shipping specific barriers. Semi-structured interviews with industry experts were used to further develop the overview of the barriers and add the required enablers. Thereafter, three case studies were conducted for additional detail, context and reflection on the theory, barriers and enablers provided by experts and literature. Pilot projects can reduce any market entry barrier for a certain vessel and operational area. These barriers can originate from interdependency, costs, uncertainty, the required assets, regulations and mindset. Pilots can significantly reduce the additional costs of climate-neutral sailing by tens of per cent, improving the market potential and 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. It has therefore been demonstrated that subsidizing pilot projects through local governments can become a key enabler for shipping, since the global nature and complex governance structure make it difficult to initiate and accelerate the transition in other ways.