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Over the last few decades, travel freedom has expanded precipitously thanks to the rising number of bilateral visa-waiver agreements and unilateral decisions of governments. While this development has likely paid significant economic dividends thanks to increased tourism, trade, and investment, has it also had any positive political externalities? The literature on democratic diffusion and globalization would suggest that expanding cross-border interactions can have a positive role in the process of democratization. Yet we have no systematic empirical evidence about the effect of the visa-waiver programs on democracy. Using an original dataset that records the number of visa-free destinations for each country from 2006 to 2018, our study offers the first cross-national analysis of this relationship. We find that the increasing number of visa-free destinations has mixed effects on the sender country’s political system.