The single most common failure in a self-planned night out abroad is misreading the last train. Not missing it — misreading it. The last train on the line is not the last train from your station, and the last train on Friday is not the last train on Sunday.
Every Kaleido route is built backwards from that time. We find the last realistic departure from the final stop, subtract twenty minutes for the walk, and that is when the evening formally ends.
If you want to keep going after that, your guide will tell you what is still open and roughly what a taxi should cost. But the plan itself never depends on you catching something you might miss.