Originally Posted by MSPeconomist

I highly recommend planning to spend an evening in Kyoto, in order to stroll through a neighborhood with geisha houses in the early evening when the geisha are out walking to work. Some of the historic buildings look special in twilight or at night too. This could be hard if you need to take a train back to your hotel in Osaka, especially in time for the lounge happy hour. Try also to see Osaka castle (perhaps from your hotel?) when it's lit up at night, although I'm not sure actually visiting the castle is the best use of time.