Autumn Engagement Celebration for First-Timers: 3-week Itinerary Check!

Hello!

My partner and I (early 30’s) are recently engaged, and to celebrate (also we were already planning this, but it has a new purpose now 🙂 ) we are fulfilling lifelong dreams and traveling to Japan for the first time! We will be there just shy of 3 weeks from late October through mid-November, and splitting our time as follows:

Tokyo > Hakone > Osaka > Kyoto > Tokyo

We are SO excited!

It’s really important to both of us that we strike a balance between doing the things we want, and having scheduled down time to just explore our surroundings, enjoy the autumn foliage, get lost. We have most things hotel-wise booked (sans our Disney resort), but everything is shiftable as needed until September. In addition to a few specific questions below, I’d love feedback on if the things we have planned make sense from a timing and location perspective, if anything feels too packed, or if you have dining or activity recommendations in the places we will be! We love great food, music, museums, video games, coffee, nature, history, woodworking, theatre, animals, theme parks, anime, and really lots of other things. I’m a big planner, so I definitely don’t shy away from feedback if you have any and just want the trip to be amazing.

Something we are trying to be mindful of: my partner broke his hip in a car crash this last winter. He’s recovered but gets sore easily, so we are making plans with the understanding that we may need to head back early some days, he may need to rest while I go out occasionally, etc.

Budget isn’t a huge factor for us (though not non-existent), and we are happy to pay a bit more for a great experience whether that be dining, hotel, etc. Alright, here we GO:

**Day 1 – Tokyo (first hotel: Shinjuku)**
Fly LAX > HND via JAL; Land around 5:30pm
Grab suica card and e-sim cards for each of us in the airport
Private transfer car to hotel
Grab something fast/easy to eat nearby or in hotel and crash

**Day 2 – Tokyo (Shinjuku/Shibuya)**
Jetlag recovery
Morning/Afternoon: Explore Shibuya and Shinjuku (options to choose from depending on how we are feeling):
-Shibuya Sky tree/scramble
-Shinjuku Gyoen National Garden
-Waseda University Tsubouchi Memorial Theatre Museum
-General walking around and exploring
Evening:
-Golden Gai

**Day 3 – Tokyo (Arakawa, Setagaya, Nakano)**
Morning:
– Ramen & Gyoza cooking class booked in Arakawa
– Head back to Shibuya for Nintendo store and Kigumi woodworking museum
– Chill and explore at/around hotel
Evening:
– Nakano Broadway
– Either stay in Nakano or go to Setagaya for live music at a couple of venues we found and dinner/drinks

**Day 4 – Tokyo (Ghibli, Disney)**
– Ghibli Museum (hoping to get in first thing at 10 when it opens)
– Pack up suitcases and ship them to next main hotel in Ginza, and pack overnight bags for 2 nights at Disney
– Head to Disney, drop bags/check into Tokyo Disneyland hotel, and use an evening ticket to enjoy Tokyo Disneyland

**Day 5 – Tokyo (Disney Sea)**
– Disney Sea all day

**Day 6 – Tokyo (Ueno/Ginza)**
Morning/Afternoon:
– Check out of Disney
– Hit teamLabs Planets on our way back into the city proper
– Drop our bags and head to Ueno
– Ueno park for a picnic and exploring
– Hard Off & Hobby Off
Evening:
– Hibaya bar whiskey (or another bar) for drinks and get dinner
– Hopefully catch a Kabuki show!

**Day 7 – Tokyo (Akihabara)**
Morning/Afternoon:
– Mostly open day (intentionally)
– Sleep in and take the train up to Asakusa and explore, Senso-ji, etc
– Go to Akihabara when we are done there for arcades, shopping, etc
Evening:
– Explore Akihabara/Ginza

**Day 8 – Tokyo (Nikko)**
– Get up early for a day trip to Nikko
– Toshogo, Kegon Falls, enjoy the national park and autumn leaves!
– Head back for dinner in Ginza

**Day 9 – Tokyo > Hakone**
– Send luggage to Osaka hotel in the AM, and pack backpacks for 2 nights in Hakone
– Use this morning to get to anything above or extra that we missed/didn’t get a chance to do
– Romancecar to Hakone and check into Ryoken (or drop bags)
– Evangelion shop
– Enjoy a leisurely evening in Ryoken

**Day 10 – Hakone**
– Ropeway
– Open air museum
– Lake Ashi boat tour if time
– Evening in Ryoken

**Day 11 – Hakone > Osaka**
– Enjoy Hakone a bit before we leave, maybe take a quick hike
– Shinkansen to Osaka, check into hotel near Dontonbori
– Pokemon Center
– Dontonbori, Scheduled bar hopping/night food tour

**Day 12 – Osaka (Universal)**
– Get up early and head to USJ for the day!

**Day 13 – Osaka > Kyoto (Himeji, Kobe)**
Morning:
– Store luggage in Osaka station
– Himeji castle
Afternoon:
– Tekenaka carpentry tools museum
– All you can eat Kobe for lunch/early dinner
– Train to Osaka to grab luggage, train up to townhouse rental in Kyoto (staying in Gion)
– Dinner near townhouse, unpack

**Day 14 – Kyoto (Gion)**
– Keep day open
– Get bikes rented for the week
– Explore temples and shrines near our townhouse (yasaka-jinja, Ryoken kannon, etc)
– Grocery shop
– Nikishi market that evening

**Day 15 – Kyoto (Naoshima OR Kinosaki Onsen)**
– Day trip either to Naoshima
OR
– Day trip up to Kinosaki Onsen for Onsen-hopping and relaxing

**Day 16 – Kyoto (Fushimi Inari, Central Kyoto)**
Morning:
– Fushimi Inari
– Unagi restaurant for lunch
– Rengio-In
Afternoon/Evening:
– Manga museum
– Open evening

**Day 17 – Kyoto (Nara)**
– Early train ride to Nara for deer, Todai-ji, Horyuji temple (if time)
Evening:
– Karaoke, find really great whiskey

**Day 18 – Kyoto (open day)**
No hard plans mostly (staying this way), but potentially:
– Arashiyama
– Sannenzaka
– Bike around town
– Find an Onsen
– Enjoy autumn leaves at Bishamon-do temple
– Shop
– Scheduled tea ceremony participation this afternoon

**Day 19 – Kyoto > Tokyo**
– Send luggage (or do this the day before?) To final Tokyo hotel in Ginza
– Do any final shopping etc in Kyoto that we want to do
– Shinkansen to Tokyo
– No plans! Just last minute shopping, fitting whatever we missed in, etc

**Day 20 – Tokyo > LAX**
No plans! Just last minute shopping and sightseeing before our flight
Fly out of NRT via Singapore Air at 6:15pm

Now a few questions!

1. I’m considering moving our south-Shinjuku hotel to Shibuya, as I’ve read it’s a bit less hectic to stay in. Do you think it’ll make a difference? The current hotel is directly the west of Shinjuku station if that helps.
2. We would really love to catch a festival or two while we are there. Any recommendations?
3. My partner has Celiac disease. We have been finding and saving as many gluten-free bakeries, restaurants etc as we can find and searching this subreddit, but we’d love recommendations if you have them!!
4. How early do we need to send luggage from city to city? For instance, for my final transfer from Kyoto to Tokyo, should I send it the day before we leave?
5. PLEASE share your must-do restaurants in any of the locations we will be in. We are fine having to make a few reservations if it’s nicer/busy.

Thanks in advance for any thoughts/feedback!