With the world moving toward sustainability, it has become necessary to employ smarter and more efficient ways of utilising the available resources. One such way to optimise resources is through public transport. A significant part of everyone’s day-to-day life is going digital, smarter, and intelligent, and transportation is no exception. In the present work, we provide an in-depth investigation into the semiotic expression of Indian children (aged 5–14 years) regarding Intelligent Transportation Systems (ITS), their perceptions, interpretations, and emergent behaviors. Set within the distinct socio-cultural, infrastructural, and sensory urban and semi-urban landscapes of India, the study employs a semiotic lens to decipher the signs, symbols, and meanings that children associate with emerging transportation technologies. These are, but are not restricted to, GPS navigation voice, ride-hailing application user interfaces, QR-coded ticketing, automated metro interfaces, Electric Vehicle (EV) charging stations, and traffic control icons. The study reveals a multifaceted semiotic ecosystem through a multimodal approach, which brings together ethnographic observations, visual elicitation, draw-and-tell activities, and focused group discussions in four cities in India. The results indicate that children’s interpretations are highly mediated by indigenous cultural metaphors (such as personification of cars as jaanwar or animals), family-level movement practices, and stark differences between high-tech enclaves and reality on the streets.