Literary tourism is a special form of tourism that falls under the category of Special Interest Tourism and cultural tourism and presents a significant increase in market share—especially during the last decade. Various destinations globally utilize their specific characteristics and offer tours and experiences related to activities such as visits to places associated with authors, places that serve as the backdrop for literary works, literary parks, literary trails, literary festivals, and bookstore tourism. The scope of this paper is to examine the level of the development of literary tourism in Greece and its connection with cultural tourism. A quantitative survey was conducted to investigate the perceptions, expectations, and motivations of Greeks regarding this type of tourism. The methodological tool used was a structured questionnaire, which was answered by 145 individuals. Additionally, the authors conducted semi-structured interviews with literary-festivals’ managers to highlight problems and prospects for this type of tourism. The results showed literary tourism is underdeveloped in the Greek tourism market but on the other hand, there is a significant potential for its development. Moreover, several demographic characteristics of the visitors have an impact on their perceptions for literary tourism activities. The results of the research enrich the understanding of literary tourism and are particularly useful for the development of policies to promote it at a destination level.