Urban experimentation has been increasingly applied as an urban development tool for finding new ways to face grand societal challenges, as they unfold in cities⁠. Experiments might trigger systemic change, since they differ conceptually from conventional urban development, as they can be radical in ambition, limited in scope, and place emphasis on learning from real-world interventions⁠. However, while there seems to be a common understanding of the importance of learning through urban experiments, there seems to remain a lack of, or unclarity on, learning and reflectivity in the practice of urban experimentation⁠. This paper aims to provide principles for developing more explicit, testable, and improvable learning strategies in urban experimentation by addressing the following question: How to foster learning for transitions through urban experiments? For this, insights from transition studies and experiential learning theory (Kolb, 1984) were used, resulting in a synthesized strategy for learning for transitions through experimentation⁠.