The main aim of this study was to evaluate the tour guiding profession by taking it together and associating it with entrepreneurship, and to determine at which stage of the tour guide’s career and in which areas opportunities for entrepreneurship may be more favorable. Based on this aim, the semi-structured interviews with 12 guides-entrepreneurs in different areas were conducted. The data collected through interviews was analyzed using content analysis methodology. One of the main findings of the research is that self-employed tourist guides can be considered as “cultural entrepreneurs”. It has been determined that the stages of “Maturity in the Profession” and “Development in the Profession” are most appropriate to start entrepreneurship. The most appropriate areas for entrepreneurship within the tourism industry where tour guides can be successful entrepreneurs have been determined as travel agency business, hospitality business and food and beverage (restaurant) business. Non-industry business where guides can be successful have been determined as areas requiring foreign languages, foreign trade, promotion and marketing areas and areas related with human relations. Another important finding of the research is that the crises in the tourism sector are seen as an opportunity by the guides to turn to different areas and to bring their entrepreneurial characteristics to the forefront.