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Over the last few years, advanced digital applications have become available to tourists. Some of these offer the possibility of creating personalised routes. This paper introduces a tourist expert system, called the City Trip Planner, that allows planning routes for five cities in Belgium. It is implemented as a web application that takes into account the interests and trip constraints of the user and matches these to a database of locations in order to predict personal interests. A fast and effective planning algorithm provides an on-the-fly suggestion of a personal trip for a requested number of days, taking into account opening hours of attractions and time for a (lunch) break. The expert system is discussed in detail. Usage statistics and user feedback demonstrate that it is highly appreciated by tourists.