This chapter focuses on the challenge of implementing sustainable urban plans and strategies for our cities and regions. It discusses some of the traits of successful plans and strategies with projects identified through case studies and informed by interviews with several leading decision makers and key stakeholders. The chapter seeks to explore the lessons learned from implementing major urban initiatives and the key elements required to provide and enable a sustainable planning system for a complex urban system operating within planetary boundaries. Sustainable pathways can be seen as the medium for connecting the key elements necessary for more sustainable cities and regions. Pathways can include the wide range of approaches from policy levers and frameworks (economic, social and environmental) to urban design and land use planning. The connections among these pathways are considered critical to success. For example, investing in the preparation of integrated metropolitan plans provides the framework and context for decision-making both in the short and long terms. Without a plan the door is open for ad hocery at best and corruption of the planning and development process at worst. Experiences in implementing plans and strategies are informed by a series of interviews of key stakeholders and urban leaders. Drawing on earlier OECD research, the positive role of national sustainable development strategies is highlighted in facilitating local action: policy integration, intergenerational time frame, analysis and assessments, coordination and institutions, local and regional governance, stakeholder participation, indicators and targets, monitoring and evaluation. This chapter concludes that it is timely for national sustainable development strategies to be reviewed, or initiated as the case may be, in light of the suite of recent global agreements for a more sustainable future.