This study examines recent developments in destination assessment and certification as a basis for identifying challenges and benefits they engender, from tourist and tourism organizations’ perspectives. It uses online surveys and semi-structured interviews to collect primary data from prospective tourists and key informants on destination assessment and certification. The findings highlight the strengths and weaknesses of schemes currently in use, including various factors that might influence their future development. Specifically, the study finds that destination assessment and certification are affected by four key issues, namely, practicability, reliability, visibility, and (un)availability of incentives. It concludes that the manifestation of these issues and their ensuing complexity affect the way in which tourists and tourism destinations engage with destination assessment and certification. This, therefore, delimits the inherent opportunities and constraints within such schemes.