First solo trip Japan, itinerary advice pls!

In December, I will be visiting Japan alone for the first time and the last time I went was 8 years ago with my parents when I was still young. My trip will span from 13th December to 26th December, my itinerary is as follows(I plan to bring 1 large backpack (Unknown volume), 1 duffle bag (38L volume) and 1 day bag which will be my carry on):

Singapore to Nagoya: 1:20AM (Local time) -> 8:30AM (Japan time)
Nagoya to Singapore: 10:20AM (Japan time) -> 4:15PM (Local time)

Day 1 (13th): Flight lands in Nagoya at approximately 8:30 AM in the morning at Chubu Intl Airport. Upon landing I will be taking the Shinkansen straight from Nagoya station to Kyoto and will be checking into my hotel which is relatively near the station.

Day 1-4 (13th-16th): I will be exploring a few areas, yet to decide which days will be spent doing what but I do plan to take 2 day trips to Osaka VIA shinkansen, here's my bucket list of places I plan to visit so far (Still yet to add more places!)

Osaka:
Shitennoji Temple
Osaka Tenmangu Shrine
Osaka Castle (Osakajo)
Katsuo-ji

Kyoto:
Fushimi Inari Yotsuji
Kiyomizu-deraHigashiyama District
Tenju an
Nishiki market
Hokokuji temple
Donguri Kyowakoku (Ghibli Store)
Eikando zenrinji temple

Day 5 (17th): After checking out of my hotel, I will be heading to Kyoto station and will be taking a Shinkansen from Kyoto station straight to Tokyo station and will then switch to the Yamanote line to get to my AirBNB.

Day 5-8(17th-20th): I have yet to decide which day will be dedicated to which activity but I do plan to take 1 day trip to Fujikawaguchiko, here's the bucket list of places I plan to visit for Tokyo and Fuji:

Fuji:
Kosaku kawaguchiko
Chureito Pagoda
Arakurayama sengen park
Lake kawaguchi

Tokyo:
Akihabara Electric Town
Shibuya city
Gotokuji Temple
Hie shrine
Senso ji
Shibuya sky (Book 1 month in advance)
Shiba park
Frites Bruges Asakusa
Harajuku chillweeb
Animate ikebukurou
Tsukiji fish market
Gyukatsu motomura

Day 9-13(21st-25th): I will be travelling to Sapporo via 2 options listed below, I don't have much planned yet but I do plan to visit Otaru and Jozankei via the bus or Hakodate line.

On the 21st and 25th, I am conflicted over these 2 options:

  1. Take the Shinkansen from Tokyo straight to Hakodate and then to Sapporo (10h~ journey) on the 21st and again Shinkansen from Sapporo straight back to Nagoya on the 25th (11h~ journey) and stay out overnight, leaving my baggage in a locker and take the first train to Chubu Intl Airport, this would require me to buy the JR pass as it would then make my journey worth
  2. Don't get the JR pass, buy the shinkansen tickets individually using the Suica card for the rest of the public transport on local lines and busses etc. Take a domestic flight from Haneda on the 21st to Chitose Intl Airport and take the rapid transport straight to Sapporo station. The current flight I'm looking at is a JAL flight from Haneda to Chitose @ 2:30PM-4PM, I will probably be at the airport by 1:30PM to be safe. The flight back from Chitose to Chubu Intl Airport is another JAL flight @ 2:10PM-4:05PM. I will be at Chitose by 1PM to be safe. Both flights come with 20KG of check in baggage for free which SHOULD be enough.

The 2nd option would save me a lot of time and is slightly cheaper than the JR pass itself for 2 weeks (around $700+ Singapore Dollars/$520+ USD) but I'm not sure if it's worth the hassle? I've never travelled solo before and have also never taken a domestic flight before. Please give your thoughts and advice and thank you!

by BirdyLikesMen

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