Tokyo/Hakone/Kyoto Itinerary check & general questions.

My partner and I (38M/F) are heading to Japan for our first trip on the 18th. We're both very excited, especially for the food! Hoping our itinerary makes sense for the time we have. I've baked in a lot of free time to just wander and eat.

Tokyo:
Tue 19th – Travel Day
– Check in around 10:30pm
– Go out to eat and drink near by

Wed 20th – Shinjuku/Shibuya
– Shibuya Nonbei Yokocho business park
– Wander Harajuku
– Memory Lane
– Golden Gai

Thur 21st – Ginza/Asakusa
– Coffee shop in Ginza
– Art Aquarium museum
– Hit & run on Tsujiki outer market
– River cruise to Asakusa
– Kappabashi Hondōri Shopping area
– Nakamise Shopping area

Fri 22nd – Free time
– Double back on any spots we'd like to spend more time in or shove in a half day trip somewhere

Hakone:
Sat 23rd – The tourist loop
– Forward baggage to Kyoto station
– Romancecar to Hakone
– Breakfast at Miharashichaya Utsuski soba shop
– Hike to Hakone Amazake Tea House for tea and snacks
– Finish hike to the lake
– Lake Cruise
– Ropeway
– Owakudani black egg for Sam
– Open Air Museum?
– Check into the ryokan, soak, relax, clean up
– Dinner in our room

Sun 24th – Train to Kyoto
– Breakfast in the ryokan
– 11:00 Wander Odawara station
– 12:00 Bullet train to Kyoto
– Wander & shop after bag pick up and check in

Kyoto:
Mon 25th – Downtown Kyoto
– Pontocho Alley
– Nishiki market
– Kyoto Sanjo Shopping street

Tue 26th – Arashiyama Day
– Breakfast at one of the stations
– Scenic train ride
– Carriage ride
– River cruise
– Jōjakkōji Temple
– Saga-toriimoto preserved street

Wed 27th – Northwest Kyoto
– Breakfast in Gion
– Take eBikes(?) To NW Kyoto
– Walk the Philosopher's path
– Visit a few temples
– Chocolate shop

Thur 28th – Kurama to Kibune
– Mt. Kurama cable railway
– Tsuzura-Ori foot path
– Kurama-dera Temple
– Lunch in Kifune over the river
– Wander the mountain town
– clean up then nice dinner out

Osaka/Oahu
Fri 29th pt 1 – Osaka
– Forward luggage to KIX
– Yamazaki distillery
– Train to Osaka
– Aquarium
– Dotonbori
– Fly to HNL 8:45pm

Fri 29th pt 2 – Honolulu
– Arrive 10:00am
– Wander & loaf

Sat 30th – Fly home

On top of just being curious if our itinerary looks too light or maybe even too packed we also had some basic questions about our trip.

1.) I am having a hard time confirming our luggage forwarding plans. Since we are staying in guest houses we dont have anyone to accept or hold bags at a front desk for us. I'm assuming that we can drop our bags off at a transfer company's storefront at Shinjuku station that will send our luggage to Kyoto station for pick up after our 1 day Hakone trip, but I am struggling to find somewhere that can pick up our luggage in Kyoto either from a konbini or at Kyoto station that will get our bags to KIX same day. Has anyone done this that can recommend which company they went through?

2.) Is the hike between Kurama to Kibune doable for someone with a bad back and someone else with not great knees?

3.) Any dupe recommendations for Golden Gai, Memory lane, Pontocho Alley or Shibuya Nonbei Yokocho business park? We're very big on hole in the wall areas with a bunch of stalls all packed in tight with killer food and cheap drinks, but hate the crowds and food geared towards travelers. I have been working on my reading and conversational Japanese so we are not intimidated by places not set up for English speakers. I get this is probably a super common ask, but on the off chance someone does have suggestions I had to try.

4.) Any recommendations on where we could find fugu nigiri instead of a big multi course meal about it? I've heard its a rather unimpressive experience but its still on my bucket list and I'd rather not dedicate precious stomach real estate to it when there is so much more to enjoy there.

5.) On that note, any recommendations for the best Chawanmushi in any of our destinations? Its my absolute #1 favorite food on the planet and I literally want to eat it everyday.

If you made it this far thank you for taking your time to read my post and helping us have the best trip we can!

by suzy9mm