Traveling is an inherently stressful endeavor and trying to maintain a secure computing environment while traveling seems like an impossible task. In our talk, we introduce a physically small, cheap, and portable security stack. This stack provides an environment with consistent structure and services while allowing users to easily plug-and-play new client devices. It has a small form-factor which is easy to move, making it ideal for travel, and can easily be expanded with new services. The aim of Armadillo is to make security on the go easy, even while using filthy and dirty hotel Wi-Fi, all while providing the user with access to the services they rely on.