With smart phones, smart cities, and endless tools to maximize efficiency and minimize travel time, the possibility for serendipitous encounters or discoveries is diminishing. Artist and architect Mark Shepard created Serendipitor, an iPhone app that brings out the playful explorer in all of us. Users input their selected destination, and Serendipitor provides inventive directional routes and suggested actions inspired by Fluxus, Vito Acconci, Yoko Ono, among others, helping users find something surprising and new along their way. Users can increase or decrease the complexity of the route, depending on how much time they have. Serendipitor is part of Shepard’s larger project, the Sentient City Survival Kit (supported by Creative Capital), which “probes the social, cultural and political implications of ubiquitous computing for urban environments.”