When searching for flights, current systems often suggest routes involving waiting times at stopovers. There might exist alternative routes which are more attractive from a touristic perspective because their duration is not necessarily much longer while offering enough time in an appropriate place. Choosing among such alternatives requires additional planning efforts to make sure that e.g. points of interest can conveniently be reached in the allowed time frame. We present a system that automatically computes smart trip alternatives between any two cities. To do so, it searches points of interest in large semantic datasets considering the set of accessible areas around each possible layover. It then elects feasible alternatives and displays their differences with respect to the default trip.