Olive is an introverted young woman who has never ventured more than four hours away from home, nor has she ever had the desire to do so. Olive is stunned when her struggling-to-make-ends-meet single mother passes away, leaving her a trust fund, with the stipulation that in order to receive her inheritance, Olive must get out of her box and explore the world. These are the stories of Olive's adventures, the extraordinary places she visits around the globe, and the array of interesting people she meets along the way, as well as some unavoidable sticky situations she occasionally finds herself in.