Start in Tokyo and leave from Kansai Airport. Between those flights, the route crosses Nagano’s inland mountains and the Sea of Japan coast, with different things to see in each place. Nagano brings Zenkoji’s pilgrimage streets and a day with the macaques at Jigokudani. Obuse adds Hokusai’s paintings and a chestnut-rice lunch. Kanazawa follows with seafood, garden craft and a museum built around reflection; Kyoto closes the trip with Arashiyama.
Choose mid-January through February if the snowy monkey-park walk is your main reason for travelling. That also puts the trip beyond the New Year closures that disrupt several stops. Snow depth, animal appearances and train services still depend on the day’s conditions. You’re planning a city-and-countryside trip, with one forest walk, rather than a ski holiday.
The three Nagano nights are all in the city. A station-area hotel gives you the east-exit bus to Jigokudani, the separate Nagaden railway for Obuse and a straightforward departure for Kanazawa. You’ll spend more time commuting to the monkey park than guests in Shibu Onsen, but you’ll avoid another hotel move. Choose the onsen town instead only if bathing and a traditional inn matter more than the Obuse outing.
Tokyo has just one full sightseeing day here. Hamarikyu, Tsukiji and Ginza fit together geographically, so you can enjoy a garden and a proper lunch without crossing the capital repeatedly. Two nights in Kanazawa leave an arrival afternoon for the market and a full day for the garden and museum. Kyoto receives the same amount of time: enough for a central evening and Arashiyama, while keeping the airport departure simple.
Book this route if you enjoy looking closely at a few places: Hokusai’s festival-float paintings in Obuse, the ropes supporting Kenrokuen’s pine branches, or the changing view across Tenryuji’s pond. Ten days won’t cover all of Tokyo or Kyoto, and the schedule leaves neither room for Takayama nor time on the ski slopes. Those are choices worth making before you buy the flights.