Climate resilience is increasingly an attribute of competitive global cities. Cities that are most responsive to change will continue to prosper. To achieve this, governance structures and decision-making approaches that promote flexible and/or robust adaptation action are required. This thesis introduces a framework for urban adaptation planning that links medium-term risk management with the development and appraisal of long-term adaptation pathways. A long-term plan informed by the appraisal of a range of plausible pathways provides the opportunity to retain the flexibility to respond to future uncertainties, whilst also demonstrating how a city could manage future climate risk. This provides stakeholders with confidence that long-term risk is adequately considered, even if there is not a need to act immediately. To demonstrate how adaptation pathways can support adaptation decision-making in an urban system, the approach and methods developed as part of this thesis are applied in London. Adaptation pathways in response to water scarcity, surface water flood and heat risk were developed, and their appraisal presented as pathways diagrams. These diagrams provide a visual representation of the sequencing of decision points and plausible adaptation actions that may be implemented in the future. Pathways diagrams present climate risk and adaptation information for decision-makers in a salient and actionable manner. The pathways responding to individual risks in London are then brought together to demonstrate how an integrated assessment framework may be used to appraise city-scale adaptation pathways that respond to multiple climate risks. The growing emphasis within adaptation planning on approaches that can react flexibly to change increases the need to better understand the dynamics of climate risk and embed learning about the effectiveness of adaptation actions. To complement the pathways and adaptation decision-making research presented in this thesis, a framework that links adaptation monitoring and evaluation (M&E), risk assessment and decision-making is presented and explored to highlight the potential benefits of, and mechanisms for, adaptation M&E to inform and strengthen iterative risk-based adaptation planning. Demonstrated for the Thames Estuary, where concepts of adaptation planning have been pioneered but the opportunities of linking to monitoring and evaluation have not been extensively explored, we show how the framework can highlight actions and factors that are contributing to improving adaptation outcomes and those that require strengthening. This thesis contributes to the literature on urban climate change adaptation planning under conditions of uncertainty. This thesis also contributes to the evidence base needed to justify long-term planning and realise the benefits of climate risk reduction through the implementation of flexible, long-term integrated urban adaptation plans.