The workcation, wherein people combine work with vacation, is a concept that originated in the United States and Europe with the spread of information and communications technology (ICT). Although it is considered a workstyle for independent people as epitomized by freelancers and the like, in Japan, the term has come to convey something different from its original meaning, taking a unique direction in which some types of training programs are referred to as workcation. How did this change come about? This study, based on surveys of three regions, examines the origin and development of satellite office workcation and learning workcation to ascertain the following. (1) In Japan, people with workcation are assumed to be employees. (2) Therefore, the workcation is heavily influenced by local governments' intentions (wanting to associate with exchange populations) and companies' intentions (it is difficult to dispatch employees to outlying areas without a work-related purpose). (3) Therefore, the workcation has evolved into something that aims to enhance creativity, learning, and introspection through close ties with communities.