The connection between rural tourism and literary tourism, with a particular focus on entrepreneurship practices, lacks a deeper study in its varied intersections and dynamics. This paper considers these relations, within the limits of potentiality and inherent risks, taking as a best practice example a non-profit organization based in the north of Portugal. At stake here are concepts such as literary tourism, rural tourism, lifestyle entrepreneurship and local sustainable development, focusing specifically on the use of local resources, with local impact, to create a differentiated offer in order to target a niche market. Rural tourism entrepreneurship, highly motivated by lifestyle aspirations, born out of literary heritage, can be sustainable and result in innovative products embedded with endogenous resources, with a significant positive socio-economic impact on the local community.