Japan: Our Two Week Itinerary
Two Weeks in Japan
Our real 14-day Tokyo, Kyoto, Nara and Osaka itinerary: the hotels, the restaurants we'd fly back for, the experiences worth booking, and the mistakes we'd skip next time.
We ate at one restaurant in Kyoto three nights in a row. By the third night the staff remembered us, and I was ready to take a part-time job there. I even had my own Japanese knife. More on that in a minute.
Chai and I just spent two weeks in Japan, and this is the full plan: a 14-day Tokyo, Kyoto and Osaka itinerary with a Nara day trip, built for comfortable pacing because Japan involves a lot of walking and stairs. You'll get our hotels, how we got around, our must-do experiences, the food we're still dreaming about, which city we'd cut if you only have time for two, and the one planning trick that saved us when the summer rain showed up.
01Our Japan itinerary at a glance
We traveled in early summer, from late June to July 10, during the rainy part of the season. Roughly five nights in Tokyo, five in Kyoto and four in Osaka.
| Days | Where | Highlights |
|---|---|---|
| 1 | Tokyo | Arrive, check in to Tokyu Stay Ikebukuro |
| 2 to 5 | Tokyo | Ikebukuro, Shibuya night photo shoot, Shinjuku, shopping, Ichiran ramen |
| 6 | Tokyo to Kyoto | Tokaido Shinkansen, check in to Agora Kyoto Shijo |
| 7 | Kyoto | Fushimi Inari (go early) |
| 8 | Kyoto | Kimono and tea ceremony at Maikoya Nishiki |
| 9 | Kyoto | Knife-making experience |
| 10 | Nara | Nara Park, Todaiji, clay-pot kamameshi |
| 11 | Kyoto to Osaka | Train to Osaka, check in to Hiyori Hotel Osaka Namba Station |
| 12 to 14 | Osaka | Namba and Dotonbori, Daruma temple, sumo experience |
| 15 | Osaka to KIX | Nankai Rapi:t to Kansai Airport (about 40 minutes) |
02Our strategy: hotels, trains and luggage
We kept it simple: one hotel per city, no daily packing and unpacking. Each hotel sat next to a station, which matters more in Japan than almost anywhere.
- Suica card for local trains and buses. Load it, tap in, ride, tap out.
- Tokaido Shinkansen from Tokyo to Kyoto, regular trains from Kyoto to Osaka.
- Luggage forwarding between cities. Our 20 kg suitcases traveled separately while we rode the train like civilized people. Best travel decision of the trip.
03Tokyo: beautiful chaos
Chai summed up Tokyo in one word: chaotic, in the most beautiful sense. Big buildings, crowds, and a ton of lights. You can't take a bad picture there. ▶ 0:16
Where to stay: Ikebukuro
Tokyo's 23 wards each have their own personality. Chai's favorite was Ikebukuro, our base: very walkable, convenient, and a little slower than Shibuya (my favorite, where we did a nighttime photo shoot). ▶ 0:49
Our hotel, Tokyu Stay Ikebukuro, was small but beautifully laid out. Our "research" on Tokyo hotels mostly confirmed that the rooms are tiny, so this one was a nice surprise. ▶ 1:40
Shopping
Chai went straight for Onitsuka Tigers. I'm convinced you can't legally leave Japan without a pair. ▶ 2:31
Where to eat in Tokyo
- Yellow: Chai's pick. A super soft, wiggly omelette over fried rice. Expect a line, and note the line continues into another alley. Yes, that's me standing in the rain. ▶ 2:49
- Ichiran Ikebukuro: my favorite. You eat ramen in your own little booth, like taking a test. Perfect for introverts, and a convert for Chai, who doesn't even eat ramen. ▶ 3:21
04Kyoto: the one that felt like home
Kyoto is the best of both worlds: temples and tradition with a slower pace, but still a real city. Of everywhere we went, Kyoto is the place I could see us retiring. ▶ 4:56
Must-do experiences in Kyoto
- Fushimi Inari: go early to beat the crowds, and decide ahead of time how far up the mountain you'll climb.
- Knife-making: you pick each part, help assemble it and even help forge it. I came home with a Santoku I love, and I'm still too scared to sharpen it. ▶ 5:44
- Kimono and tea ceremony at Maikoya Nishiki, then a walk past the temples in our kimonos. Chai's favorite day of the whole trip. We got lost, and it was still perfect. I was hesitant, and I'd do it again. ▶ 6:31
Kyoto also has great specialty shops. I lost some time in the vintage and secondhand camera stores. Buses are easier to use here than in Tokyo. ▶ 7:04
Where to eat in Kyoto
- Tai Sushi: a tiny ten-seat local spot near Nishiki Market, off the main drag. Sushi as big as Chai's hand (she has small hands, but still). Best sushi we've ever had, especially with a Sapporo. ▶ 7:20
- Yakiniku Daisuke: my favorite restaurant on the planet. Otherworldly food, and a chef and staff who joke with each other and with you. We went three nights in a row. ▶ 8:08
Where to stay in Kyoto
Agora Kyoto Shijo was our biggest room and, I think, the least expensive. Close to Shijo and Karasuma stations, a bus stop, and conveniently across the street from Yakiniku Daisuke. The whole bathroom is a Panasonic unit, floor to ceiling. It's like showering inside an appliance, and it was awesome. ▶ 8:57
05Nara day trip
Nara Park and Todaiji are a classic day trip from Kyoto. Lunch was the highlight: Kamameshi Naraya, where rice cooks in its own clay pot. Try the unagi kamameshi. ▶ 11:36
Now, the famous deer. Everybody raves about them. Chai said it felt like being cornered by thugs asking for her bag. They're bold when they smell food, so keep snacks, maps and belongings close, and enjoy them from a respectful distance. ▶ 16:30
06Osaka: let's eat
We both expected Osaka to be laid back like Kyoto. Wrong. It felt busier than Tokyo, in the best way, with more tourists in the shopping areas. ▶ 9:45
Hiyori Hotel Osaka Namba Station sits right by Nankai Namba Station, which makes the airport run easy. Small but smart, bigger than Tokyo, with a foot massager in the room and a view across the expressway to a mall. ▶ 11:05
The sumo experience
Our standout in Osaka. You learn the history, warm up and train with real sumo wrestlers, then everyone gets a match. Did I win? Let's say I was helped a good bit. I would do that every single day. ▶ 12:11
We also loved visiting a Daruma temple and shrine, which made a peaceful break from the Dotonbori crowds.
07Best and worst of the trip
| Category | Our pick |
|---|---|
| Restaurant we'd fly back for | Yakiniku Daisuke, Kyoto (we both agree) |
| Favorite hotel | Agora Kyoto Shijo, for space and walkability |
| Favorite city | Kyoto, for both of us |
| Chai's favorite experience | Kimonos around Kyoto's temples |
| Joe's favorite experience | Sumo in Osaka |
| Best purchases | Chai: a bag for our second anniversary. Joe: a fisheye lens, now earning its keep in my thumbnails. |
| Least favorite | Chai: the Nara deer gang. Joe: arriving too late to enjoy the Godzilla head in Shinjuku (my fault). |
08Only time for two cities?
We'd both skip Osaka, for now. If you've never been to Japan, you kind of have to see Tokyo, and Kyoto is the perfect change of pace. Osaka probably deserves another visit from us, though. Chai already said she'll prepare her visa. ▶ 17:37
09What we got right, and what we'd change
Right: planning with AI
Chai built our day plans with ChatGPT, balancing activities by energy and heat. When the summer rain hit, we asked it to reshuffle the schedule on the fly. Any AI works: ChatGPT, Claude, Gemini or Perplexity. ▶ 19:12
Want the same setup? Grab my free Japan trip AI planning template. Fill it in like a Mad Lib, paste it into your favorite AI, and you've got a custom itinerary.
Wrong: trusting the plan over the map
We got lost a few times, mostly on buses, because bus codes for each direction can be confusing. Once you're on the move, switch to Google Maps for the most current bus and train details. ▶ 20:34
10What does two weeks in Japan cost?
Japan isn't cheap, but it's better value than most people expect. I broke down our hotels, food, trains and experiences in a separate video:
And if you're wondering whether a trip like this could turn into something longer, start with my Retire in Japan hub and the foreign retiree's guide to taxes in Japan.
Frequently asked questions
Is two weeks enough for Tokyo, Kyoto and Osaka?
Yes, at a comfortable pace. About five nights in Tokyo, five in Kyoto with a Nara day trip, and four in Osaka gave us time for booked experiences plus unplanned wandering.
Where should I stay in Tokyo, Kyoto and Osaka?
Stay near a major station. We used Tokyu Stay Ikebukuro in Tokyo, Agora Kyoto Shijo in Kyoto and Hiyori Hotel Osaka Namba Station in Osaka, which also made the airport train easy.
How do you get between cities in Japan?
Take the Tokaido Shinkansen between Tokyo and Kyoto and regular trains between Kyoto and Osaka. Use a Suica card for local transit, and forward big suitcases between hotels.
If I only have time for two cities, which should I pick?
For a first trip, Tokyo and Kyoto. Tokyo is the big-city experience and Kyoto adds temples, tradition and a slower pace.
Are the deer in Nara dangerous?
They aren't dangerous, but they can be pushy when they smell food. Keep snacks and paper maps out of reach and give them a little space.
More Japan videos
Your Best of Japan
What's your must-do in Japan? Or which city would you skip? Tell us in the comments below or on YouTube. Chai and I read every one.
Subscribe on YouTubeThis is our own trip and experience. Hotels, restaurants, booking rules and prices change, so check current details before you book. Not financial, legal, tax or immigration advice.
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