Start in Tokyo and leave from Kansai Airport. Between those flights, Nagano brings Zenkoji’s pilgrimage streets, Jigokudani’s macaques and an Obuse day for Hokusai’s paintings and a chestnut-rice lunch. Kanazawa adds seafood, Kenrokuen’s winter pines and the D.T. Suzuki Museum; Kyoto closes the trip with Arashiyama.
Choose mid-January through February if the snowy monkey-park walk is your priority, beyond the New Year closures affecting several stops. Snow depth, animal appearances and train services still depend on the day. This is a city-and-countryside trip with one forest walk, without skiing.
Three nights near Nagano Station give both day trips one base: the east-exit bus reaches Jigokudani and the Nagaden railway serves Obuse. Shibu Onsen suits a holiday centred on bathing and a traditional inn instead. Tokyo has one full sightseeing day; Kanazawa and Kyoto each get an arrival afternoon and a full day. The four bases leave time for the named gardens, art and regional meals, rather than extra stops in Takayama or on the ski slopes.