It has become evident that rural tourism grew significantly during the pandemic compared to mass tourism. However, at this time, all the forecasts were wrapped in considerable uncertainty regarding travel, which is not without the elevated associated risk. Therefore, we assessed the perceptions of the entrepreneurs in relation to rural tourism activities regarding the advantages of their rural tourism activity in the Azores for customers. Furthermore, the potential for developing this typology of tourism is pivotal for obtaining very reliable data and information on this topic and enabling us to provide guidelines for the leading regional players. In this regard, an exploratory method was used to assess the perceptions of the entrepreneurs with rural tourism activities in the Azores Islands regarding the customers’ experiences and some other important aspects concerning the promotion of this type of tourism in the region. Throughout this study, it was possible to verify that the most relevant obstacles to the development of rural tourism in the Azores region are the preservation and conservation of nature and endogenous resources and delivering proper infrastructures and regional accessibilities. Contrarily, the increase in community and regional funding and support for rural tourism could be key to the prosperity of this typology of tourism in this insular territory.