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The uniqueness of Pisa tower has always been a mystery and drawn the attention. On the other hand, the revised 2013 curriculum demands the use of context which can stimulate the students to solve daily life problem. This research aimed to produce a mathematical problem by using Pisa tower as the context that is valid and practical. The method research used was design research with development studies type which consisted of two stages, namely: the preliminary and formative evaluation. The techniques used for collecting data were walkthrough, document reviews, observation, and interviews. This research involved eighth-grade students which consisting of 12 students who had various capabilities. This research produced a mathematical problem about estimating the leaning tower of Pisa. Based on the research result, the developed problem had 1) Validity regarding content, context, and language from the assessment of expert reviews and one to one, 2) Practicality that can be seen from the developed problem, could be easy to understand by students. In addition, the Pisa tower context could develop students- mathematical representation skills such as building mathematics through mathematical model, solving the problem involving mathematical expressions and making the situations based on the problem given.