The aim of this paper is to examine how the sustainability assessment of a tourism destination can be carried out while taking local conditions into account. The fact that every destination has its own features is often disregarded and a general set of sustainability indicators is used to measure sustainability in all tourism destinations. The question is, if imposing a universal system on destinations with particular features will inevitably result in a superficial analysis that disregards the specific local circumstances. The focus of this paper therefore lies in discussing approaches, opportunities, risks and challenges for the addition of contextual features into the destination assessment process. The paper is based on a case study conducted in Windhoek, Namibia. Central findings are, that the extent to which the indicator set needs to be adapted depends on the purpose of the assessment and on the characteristics of the destination. Recommendations and a refinement of the assessment methodology for the evaluation of sustainability in destinations with different local conditions are provided.