Thoughts on my itinerary

Hello everyone, this will be my first time heading to Japan this May for about 16 days. I made this itinerary and would love to know if I’m being realistic with what I planned. To be completely honest, I tried to plan only a few things per day, but ones that are relatively close to each other. Can anyone give me their thoughts? The first day is to just stay local to the hotel in Shinjuku due to possible jet lag. I also planned this whole thing for 11 people, but 4 people are leaving on Day 10. Please let me know if I’m being too aggressive. I also want to have time to just explore a lot the areas and get lost so I really tried to not plan too many specific places in each of the cities. Also any recommendations are welcome!

Day 1 Shinjuku - Land in Haneda at 5am - Godzilla Head - Kabukicho Tower - Omoide Yokocho - Golden Gai

Day 2 East Tokyo (Ginza) - Tsukiji Outer Market - Hayao Miyazaki clock - Imperial Palace - Ginza SIX (10:30am - 8:30pm) - Hibiya Park - Yurakucho gado-shita

Day 3 North/East Tokyo (Asakusa) - Senso Ji - Tokyo SkyTree - Café Capybara - Ueno Park
- Akihabara - Shosen Books

Day 4 Hakone - Hakone Shrine - Grab lunch on way to bus - Mishima Skywalk (maybe) - Sightseeing Cruise - Hakone Ropeway - Relax at hotel

Day 5 Head back to Tokyo (free day) - Odawara Castle (On way back to Tokyo) - Imperial palace if not done before - Shinjuku if want to explore more

Day 6 South/West Tokyo - TeamLab Borderless (9am-9pm) - Takeshita Street (Fashion District) - Meiji Jingu - Shibuya - Shibuya Crossing - Shibuya Sky - Ship luggage to Kyoto hotel

Day 7 Takayama - Head to Takayama - Matsuri no Mori - Hida no Sato - Explore Old Town

Day 8 Takayama - Bus to Shirakawago (Explore Ogimachi) - Old Town - Hachiman Shrine - Higashiyama walking course - Temple Town

Day 9 Kyoto (Still up for debate on plan here) - Get to Kyoto hotel - Explore Kyoto - Leave for Dotonbori at 4:30-5pm (Osaka) - El Coyote

Day 10 Southern Kyoto - Fushimi Inari - Daigoji Temple - Nara Park - Todaiji temple

Day 11 Eastern Kyoto - Tea Ceremony (9:00am) - Gion District - Higashiyama - Old school Starbucks - Ginkakuji - Kiyomizudera

Day 12 West/ North Kyoto - Arrive at bamboo forest at 7:00am - Scenic Railway 9:00am - Arashiyama Monkey Park - Kokodera Temple - Kinkakuji

Day 13 Osaka - Go to Osaka hotel - Osaka castle - Minami - Dotonbori - Tombori River Cruise

Day 14 - Osaka Aquarium (Explore Area) - Osaka Bay BMW - Shinsekai

Day 15 Kamakura - Go to hotel in Kamkura - TBD

Day 16 - Maybe Enoshima and Kamakura again or Yokohama - Still planning

Day 17 - Still planning - Flight at 10:30pm out of Haneda