Understanding tourism as a complex system is a challenge in postgraduate tourism education. The complexities of understanding tourism as a system stem from the implications for decision making in business, long-term planning, and adopting sustainability and corporate social responsibility positions. This study evaluates a series of assessment items designed around pedagogical principles of scenario-based learning, role play, and collaborative learning. Using data from end-of-semester surveys and a reflective assessment piece, 30 students evaluated the series of assessment criteria for their effectiveness in helping students to consider tourism as a complex system and how the use of iPads and wikis were used to complete the assessment tasks. Results suggest that the series of assessment tasks was useful in developing critical thinking around tourism, including how tourism is a complex adaptive system, developing collaborative learning, practicing skills useful for a career in tourism, and building teamwork, whereas the wikis and iPads were useful as a platform to support this learning.