Hey everyone! I’m sharing an updated itinerary for my upcoming trip to Japan in October. You guys have been an incredible help over the past few weeks. Here is the old itinerary from a previous post.

Last year, I visited Japan for the first time with a friend, and it was an unforgettable experience. I’m extending my stay this time and bringing my boyfriend and brother along for their first visit.

The previous trip was a valuable learning experience, helping me understand the places I truly enjoyed and the ideal amount of time to spend in each location. With five months of meticulous planning, I’m confident in my knowledge of popular and off-the-beaten-path spots.

I aim to balance showing my boyfriend and brother the highlights while exploring new areas. I’ve tried to keep this itinerary detailed yet flexible, focusing on the experiences rather than specific meals or shops, as the best finds often happen spontaneously.

About Us: We’re in our early 30s and enjoy nature walks, urban exploration, and discovering fabulous, unexpected places. We’re also foodies passionate about culture, anime, industrial design, and fashion (thrifting).

Itinerary

October 6 — Arrival in Osaka

I tried not to be overwhelmed by this day, as it was the day we would be landing, but I wanted to take advantage of it since we would get to Osaka in the morning.

- Arrive at 8 AM
- Rest and acclimate after the long flight
- Dotonbori
- Nipponbashi
🍔 Meals: Breakfast, lunch, and dinner locally
🏨 Hotel: APA Hotel & Resort Midosuji Honmachi-Eki Tower

October 7 — Nara Day Trip

I plan to take a day trip to Nara to explore some temples, admire and feed the deer, and retry this gorgeous vegan spot I visited the first time. Even though I am not vegan, it was probably the second-best thing I ate on the trip.

- Nara Park
- Tōdai-ji
- Kasuga Taisha
- Kōfuku-ji
- Naramachi
- Return to Osaka in the evening and explore
🍔 Meals: Breakfast, lunch, and dinner locally

October 8 — Kobe Day Trip

I enjoyed Kobe a lot. I wanted to go again because my brother is a big Naruto fan, so I wanted to go to Awaji Island for the Naruto park. My brother is also a lover of beef, and I wanted him to try some Kobe beef while we were there. I am including a few additional places locals recommend, like the herb gardens and Chinatown.

- Rokko Garden Terrace
- Naruto x Boruto Park
- Chinatown Nankinmachi 
- Kobe Nunobiki Herb Gardens
- Return to Osaka in the evening and explore
🍔 Meals: Breakfast, lunch, and dinner locally

October 9 — Osaka

This is our full day in Osaka, so I am ensuring I do anything else I could not do the previous days.

- Osaka Castle
- Osaka Aquarium Kaiyukan
- Umeda Sky Building
🍔 Meals: Breakfast, lunch, and dinner locally

October 10 — Kyoto

Kyoto, this time around, would be pretty much the same loop as last time; however, I am adding a few new things. I could comfortably do all the things below for this day in one day; I just had to wake up early and take short breaks between each thing.

- Kōdaiji Temple
- Ninenzaka and Sannenzaka Slopes
- Kiyomizu-dera
- Maruyama Park
- Chion-in Temple
- Yasaka Shrine
- Gion, in the evening
🍔 Meals: Breakfast, lunch, and dinner locally
🏨 Hotel: Laon Inn Gion Nawate

October 11 — Kyoto (Arashiyama)

Arashiyama might be overhyped, but I still loved it, especially when you go as early as possible. It can feel quite surreal. At this point of the trip, my body needs the total relaxation of an onsen. I truly enjoyed Tenzan no You; to this day, my favorite ‘dip’ was in their sparkling water tub—revitalizing!

- Okochi Sanso Garden
- Arashiyama Bamboo Forest
- Tenryu-ji
- Togetsukyo Bridge
- Tenzan no Yu for much-needed relaxation
🍔 Meals: Breakfast, lunch, and dinner locally

October 12 — Kyoto (Uji)

We will wake up extra early, at 5 AM, to go to the Fushimi Inari shrine. I want to experience the shrine with almost no people and for it to be a magical, meditative walk up the shrine. After the shrine, we will take a day trip to Uji, immerse ourselves in the matcha culture, and take a scenic walk by the river. If there’s time, we can come back up and do Eikan-dō Temple and the other things.

- Fushimi Inari Taisha
- Byodo-in Temple
- Explore Uji

If time permits:
- Eikan-dō Temple
- Philosopher’s Path
- Heian-jingū Shrine
- Kyoto Gyoen National Garden
- Nijō Castle
🍔 Meals: Breakfast, lunch, and dinner locally

October 13 — Kanazawa

This is a much sought-after addition to the trip that was recommended to me. I am excited to see a different part of Japan that isn’t as touristy but has a more relaxed vibe. My brother and I are fans of swords and ancient weaponry, so we are excited to visit the samurai village.

- Kenroku-en
- Kanazawa Castle Ruin
- Omicho Market
- Explore Nagamachi District
- Explore Higashi Chaya District
🍔 Meals: Breakfast, lunch, and dinner locally
🏨 Hotel: Smile Hotel

October 14 — Takayama

At this point, we started our ‘descent’ to Tokyo, and Takayama was highly recommended. I love nature and enjoy staying in a more remote area of Japan. It is an excellent way to disconnect from what’s coming next.

- Takayama Jinya
- Miyagawa Morning Markets
- Sanmachi Suji
- Takayama Matsuri Yatai Kaikan
🍔 Meals: Breakfast, lunch, and dinner locally
🏨 Hotel: cup of tea ensemble

October 15 — Gero Onsen

Total relaxation. We will stay at Yunoshimakan, where a Kaiseki meal is included. We are excited to enjoy the Ryokan onsen and the local public ones.

- Briefly explore Gero Onsen.
- Spend the rest of the day in the Ryokan relaxing.
- Enjoy the included breakfast and start the TREK.
🍔 Meals: Breakfast, lunch, and dinner locally
🏨 Hotel: Yunoshimakan

October 16 — Gero Onsen/Hakone

I know that going to Hakone from Gero onsen takes about four hours. I am still debating whether this is the smartest thing to do, but it is what I have so far. I am not here to enjoy the ryokan/onsen life; we already did that on Gero. But I do not oppose going to a bath or two while there. I am more interested in doing the loop and packing as much as possible.

- Enjoy the included breakfast at Yunoshimakan and start the TREK.
- Hakone Open-Air Museum
- Relax in an onsen
🍔 Meals: Breakfast and lunch locally

October 17 — Hakone/Tokyo

Since most things in Hakone close at 5 PM, we will go to Tokyo that day, enjoy a local dinner, and explore.

- Hakone Ropeway
- Explore Owakudani
- Lake Ashi
- Hakone Shrine
- Hakone Checkpoint
- Hakone Kowakien Yunessun

Once in Tokyo:
- Explore Kabukicho
- Explore Omoide Yokocho
🍔 Meals: Have dinner locally

October 18 — Tokyo

This is my first full day in Tokyo. Nothing is too extraneous; there are just a few key areas to visit. Since it is a big city, it is fun not to overplan and go with the flow. Since I only have two full days to show my brother Tokyo, I am going to a few key areas while optimizing my route.

- Meiji Jingu Shrine
- Harajuku
- Omotesando Hills
- Shibuya Scramble Crossing
🍔 Meals: Breakfast, lunch, and dinner locally

October 19 — Tokyo

This day is dedicated to shopping. This is my brother’s last day in Japan, so I wanted to visit some places to buy souvenirs and feel like we are exploring.

- Ueno Park
- Explore Akihabara
- Explore Ginza
- Tsukiji Outer Market
- Odaiba
🍔 Meals: Breakfast, lunch, and dinner locally

October 20–21 — Nikko

I couldn’t go to Nikko on my last trip because of some unforeseeable circumstances, but now that I have a few extra days, I want to get lost in nature. I don’t think we will stay at a Ryokan, but it can’t be too expensive if we do. I am always comfortable going to a public onsen to relax.

- Travel to Nikko
- Toshogu Shrine
- Explore Nikko’s historic and scenic spots
- Lake Chuzenji
- Kegon Falls
- Ryuzu Falls
- Nikko National Park
🍔 Meals: Breakfast, lunch, and dinner locally

October 22 — Tokyo

I call this ‘Tokyo Pt. 2’ since we are here again. I wanted to take this second part to explore other areas of Tokyo that I had yet to explore. My first time in Tokyo was rushed.

- Travel back from Nikko
- Asakusa
- Senso-ji Temple
- Explore Sumida Park and Tokyo Skytree
🍔 Meals: Breakfast, lunch, and dinner locally

October 23 — Tokyo

More Tokyo exploring!

- Tokyo Imperial Palace and East Gardens
- Roppongi
- Mori Art Museum
- Roppongi Hills
- Tokyo Midtown
🍔 Meals: Breakfast, lunch, and dinner locally

October 24 —Tokyo

It is sad to leave, but I can use this day to do some last-minute shopping. We will stay at a hotel that can store luggage and retrieve it once we are ready to go to the airport.

- Shinjuku Gyoen National Garden
- Last-minute shopping in Shibuya or Harajuku
- Depart from Haneda at 11 PM
🍔 Meals: Breakfast, lunch, and dinner locally

Questions

Context

My brother will be with me until October 20, but my boyfriend and I will stay until October 24. So, I want my brother to see more of Tokyo before he leaves.

1. Hakone Stay Duration: I initially planned to stay in Hakone for two days but have changed it to one day and one night. Considering the travel time from Gero Onsen to Hakone (around four hours), does it make sense to stay just one night in Hakone? Will this give us enough time to see the main attractions and do the Hakone loop?
2. Gero Onsen to Tokyo: I considered going directly from Gero Onsen to Tokyo but found the timing challenging. Do you think it’s better to go from Gero Onsen to Hakone first, or should I reconsider going straight to Tokyo to save time?
3. Nikko Trip: Would spending two days in Nikko make sense? I wanted to spend only a few days in Tokyo, and Nikko was recommended. Is it worth the trip, or should I allocate these days differently?
4. Tokyo Activities: For the last three days in Tokyo, I’m unsure if my planned activities make the most sense. I’ve listed some general places, but I would appreciate any suggestions or confirmations that these plans are optimal for our interests.