Cities are constantly transforming and, consequently, attracting efforts from researchers and opportunities to the industry. New transportation systems are being built in order to meet sustainability and efficiency criteria, as well as being adapted to the current possibilities. Moreover, citizens are becoming aware about the power and possibilities provided by the current generation of autonomous devices. In this sense, this paper presents and discusses state-of-the-art transportation technologies and systems, highlighting the advances that the concepts of Internet of Things and Value are providing. Decentralized technologies, such as blockchain, are been extensively investigated by the industry, however, its widespread adoption in cities is still desirable. Aligned with operations research opportunities, this paper identifies different points in which cities&rsquo / services could move to. This also study comments about different combinatorial optimization problems that might be useful and important for an efficient evolution of our cities. By considering different perspectives, didactic examples are presented with a main focus on motivating decision makers to balance citizens, investors and industry goals and wishes.