The interplay of generations cannot be overstated as an area that needs better understanding, especially in the collective societies of India, that allow for inter-generational exchange at multiple levels. Children, parents, grandparents and even great grandparents all have a say in each other's lives, with decisive impact on everything from spending habits to social, political and economic attitudes. India's multi-faceted character makes the challenge of understanding generational interplay as daunting as it is exciting. Understanding deeply held beliefs and attitudes requires more than just compartmentalised enquiries, but rather, guard-railed explorations in a truly multi-faceted environment that reflects the country itself. The key to understanding the impact of different generations on each other, lies in bringing them together in an environment that breaks away from the sanitised, simulated and heavily ‘guided' structures of focus groups and even in-home interviews. Essentially, to have an environment that reflects India - mobile, dynamic, evolving and multi-dimensional. This approach to understanding generational interplay harnesses the power of travel as an ethnographic and qualitative research experience, a socio-cultural, economic and political equalizer as the backdrop, and the innate peculiarities and uncertainties that only travel can afford.