From living museums to heritage escape rooms, edutainment is becoming a norm in heritage interpretation, yet not much is known of the specific role humour plays in the creation and performance of such educational products. This paper explores concepts of authenticity, functions of humour, and experience design dimensions in an in-depth case study of a tourism product. The product “Smart Head Primary School” is a re-enactment of teaching as it occurred in the 1950s in Slovenia. It became very popular primarily due to its extensive inclusion of humour. The product uses the role of a strict teacher to interpret to the “pupils” (visitors) the prime elements of the region’s heritage. To analyse the intertwining of humour with heritage interpretation, the authors combine two research methods: (a) a survey distributed to the visitors of the product, and (b) the in-depth analysis of a transcribed video-recording of a sample performance including the self-analysis and the reflections of one of the “teachers”. The results show that with the use of humour, visitors are able to perceive and recognize the difference between objective and constructive authenticity more effectively.