In the developed world, broad technological dominance and advances in infrastructure deployment have led to commoditized Internet access. In parallel to these trends, two developing countries from different parts of the world are making history by deploying 'state of the art' nationwide wireless broadband networks. These two nations, Macedonia and Mauritius, had nothing in common, but since early 2006, both of them will provide their citizens ubiquitous wireless Internet access. Since they will be the first countries in the world to deploy wireless networks at this scale, we seek to analyze the commonalities and differences between technology strategy, government policy choices, public and private institutions, informal citizen networks, and the broader socio-economic impacts of such deployments. In this paper, we describe how these two trajectories are novel, yet significantly different, with a potential for effecting unique types of change.