When searching for flights, current systems often suggest routes involving waiting times at stopovers or even overnight stays between connecting flights. There might exist alternative routes which are more attractive from a touristic perspective because their duration is not necessarily much longer while offering just enough time in an appropriate place: not too short nor too long. 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 two cities in the world. To do so, it searches points of interest in large semantic datasets taking into account the set of accessible areas around each possible layover. It can then elect two feasible alternatives while displaying their differences with respect to the default trip.