In many ways the island nation of Cuba and the State of Florida are remarkably similar. Both comprise similar area and similar sized populations, and until 45 years ago both were linked much more strongly than today. However despite being physically close, in economic and political terms the island nation of Cuba and the State of Florida are worlds apart. Overall, while Florida has grown ever stronger economically since this time, economic growth in Cuba has been far more constrained due to external pressures – most notably the economic blockade by the United States and the collapse of the Soviet Block. This paper devises a range of indicators for both territories to explore how mobility, energy use and emissions might be influenced by socio-economic conditions. Specifically, it compares and contrasts how transport policies have developed in an environment with virtually no economic constraints (Florida), and a situation where strong constraints were in place (Cuba).