Itinerary check + advice

Looking for advice for my upcoming travel to Japan later this year. Thusfar I have the following in mind:

19 dec 11:35 arrival Osaka

19-23 Osaka ->early morning train to Kyoto

23-27 Kyoto -> early morning train to Tokyo

27-2 Tokyo

Or

19-22 Osaka -> late night train to Kyoto

23-26 Kyoto -> late night train to Tokyo

27-2 Tokyo

Or

19- 22 Osaka -> late night train to Kyoto

23-25 Kyoto -> late night train to Tokyo

26-2 Tokyo

3 jan 00:05 departure Tokyo

Daytrips?

Hakone (from Tokyo)

Kamakura (from Tokyo)

Nikko (from Tokyo)

Uji (from Osaka)

Okayama (from Osaka)

Which itinerary would you pick? Or what changes would you make? I know the days around New Year are supposed to be quieter, hence why I am looking for advice to fill those days too 🙂

by NL_Kaleidoscope