17-Day Japan Trip in the winter: Feedback Welcome!

Hey everyone!

My bf and I (both 25) are heading to Japan for 17 days from late December to mid-January. We’re looking for a chill, relaxed trip with a mix of culture, history, and amazing food. We love jazz, so any cool bars or live music spots are a big plus.

We’re not about hitting every single iconic spot, we’d rather enjoy a few highlights, wander around neighborhoods, find good eats, and soak in the atmosphere.

We’ve put together a day-by-day itinerary (Tokyo → Kyoto → Osaka → Tokyo) and would love your thoughts: Does this look fun and doable? Any secret spots or must-tries we should add?

Here’s what we’ve got so far:

Day 1

  • Check-in at accommodation, rest a bit
  • Evening stroll around the neighborhood
  • Casual dinner at kaiten sushi near accomodation

Day 2

  • Token Hakubutsukan (samurai swords museum)
  • Walk along Sumida River, cross to Asakusa area
  • Explore traditional streets and shops in Asakusa
  • Stop at Kappabashi Street (kitchenware shopping)

Day 3

  • Visit Yasukuni-jinja Shrine and Yūshūkan Museum (military history)
  • Lunch in Chiyoda
  • Walk through Kitanomaru Park / Imperial Palace East Gardens
  • Explore Ochanomizu

Day 4

  • New Year's Eve omakase dinner (maybe Sushi Hicho, 20 min walk to temple)
  • Go to Meiji Jingu for the bell ringing at midnight

Day 5

  • Full day in Shibuya: Center Gai, Hachiko, Shibuya streets, Daikanyamacho, Harajuku, and Omotesando

Day 6

  • Tokyo Metropolitan Art Museum
  • Stroll through Yanaka Ginza
  • Evening in Omoide Yokochō for dinner at local food stalls
  • Drinks in Golden-Gai (Dug Jazz Cafe & Bar)

Day 7

  • Short morning stroll, café visit, check-out by 10am
  • Shinkansen to Kyoto (right side for Mt. Fuji view), arrival and check-in
  • Walk through Sannenzaka and Ninenzaka
  • Kiyomizu-dera at sunset (less crowded than morning)
  • Dinner in Gion

Day 8

  • Bamboo Grove (go early, before 9am)
  • Tenryu-ji Temple
  • Monkey Park Iwatayama
  • Lunch in Arashiyama
  • Sagano scenic train
  • Relaxed dinner downtown

Day 9

  • Day trip to Minoh Park

Day 10

  • Yasaka-jinja Shrine (Gion)
  • Samurai & Ninja Interactive Museum
  • Walk through Pontocho
  • Funaoka Onsen

Day 11

  • Café with a view (Mo-an)
  • Nishiki Market (street food and small shops)
  • Fushimi Otesuji Shopping Street (local vibe, not touristy)
  • Farewell dinner in Gion

Day 12

  • Check-out, breakfast in Kyoto
  • Train to Osaka
  • Check-in at accommodation
  • Osaka Castle
  • Izakayas in Kitashinchi

Day 13

  • Sumiyoshi Taisha Shrine (quiet, iconic red bridge)
  • Lunch at Kuromon Ichiba Market
  • Afternoon in Amerikamura
  • Orange Street
  • Jazz bar near Orange Street

Day 14

  • Osaka Aquarium in the morning
  • Shinsekai in the afternoon

Day 15

  • Check-out Osaka
  • Shinkansen back to Tokyo
  • Check-in in Tokyo
  • Ghibli Museum
  • Explore Kichijoji

Day 16

  • Last day: revisit favorite spots, final shopping, take it easy

Day 17

  • Check-out and head to the airport at 9am

We’ve mapped out some plans, but we know the best memories happen when you’re relaxed and in the moment. Thanks for any tips!

by Organic_Thought