Crete is a typical example of mass tourism in the Mediterranean and stakeholders are seeking solutions to mitigate mass tourism’s negative impacts. Technological and smart tourism solutions have been proposed as tools for sustainable development, though public acceptance remains a critical challenge. The study presents preliminary results from a quantitative survey of 280 permanent residents in the Chania prefecture of Crete, examining attitudes and perceptions towards technology in the context of tourism and community development. We collected the empirical data through purposive, non-representative sampling. Unlike most studies that focus on tourists, this study focuses on permanent residents across urban, mountainous, and seaside areas in the Chania prefecture. Findings show respondents exhibited higher mean scores regarding the benefits and risks of technology use in the tourism industry as far as the destination and local business are concerned. They seem to rate the effect of technology (either positive or negative) on locals at a much lower ranking. Another finding that comes strong out of the analysis relates to the fact that use/exposure to technology seems to exert an effect on the benefits associated with the use of technology in the tourism industry among locals. The results emphasize the need for targeted efforts in digital literacy, infrastructure, and trust building while highlighting the role of residents as active participants in the regions digital tourism transformation.