A quarter of energy-related greenhouse gas emissions (GHG) originate from the transportation sector. Continuously increasing demand for transportation services worldwide is one of the main urban challenges addressed by Sustainable Development Goal 11, target 2. One way to address this issue is to develop an integrated transportation system that can ensure confidence and comfort for the passengers. This will contribute not only to the customers’ experience but also to operators and authorities through sustainable, cost-effective, and profitable services. Conversely, the lack of such a system or a poorly managed system prevents the economy and society from realizing its potential. In the transition towards sustainability, the planning process of complex systems such as transportation often requires supportive tools and methods, such as futures methodologies that assist decision-making by providing information about possible futures. In today’s rapidly changing environment, forecasting tools do not always provide the expected outcomes since it is difficult to predict all the unexpected events. Therefore, there is a demand for alternative methods that not only grasp the constant changes but also create additional value (for example, meeting the needs of multisectoral collaboration and creation of common vision). The present article investigates the usefulness of three such methodologies, namely backcasting, foresighting, and SymbioCity, for the planning process of the bus park and railway station in Kisumu, Kenya, and Centralen in Gothenburg, Sweden. The paper’s contribution is a description of the Kenyan transportation system (which has not been studied in detail before), planning process, and pertinent issues related to the stations both in Kisumu and Gothenburg, located in the sharply contrasting contexts of global South and global North, respectively. On the basis of field research, interviews, and feasibility study of futures methodologies, the paper concludes that backcasting is the most suitable of the methodologies for both places, since it can be applied at a small scale, and provides creative solutions and has a high level of integration of stakeholders. Furthermore, the paper examines the application of the futures methodologies in multisectoral urban transitions apart from transportation and draws conclusion on what can be learnt from it.