It is expected that climate change will affect important natural inland waterways in Europe, among others, the Rhine River. Inland waterway transport is one of the main economic activities developed in the Rhine, and the effects of climate change on this activity are of great concern for skippers, the industry and policy-makers. This paper aims to identify whether longer and more frequent dry periods projected in the Rhine River will turn into a physical limitation that prevent inland waterway transport companies from guaranteeing reliable transportation to their customers, and – if so – when such a situation might take place. Based on the adaptation turning point approach, we propose a four step method to identify critical time periods for future climate change adaptation. According to our results, the inland waterway transport sector will start facing insurmountable problems associated with low water levels within the time span 2081–2095. The adaptation turning point approach provides analysts with a dynamic appraisal method that allows options to be ranked with timing of period of effectiveness and the time span needed for implementation as criteria. This increases flexibility of planning and allows for uncertainty about changing future conditions.