2 Week Trip Itinerary Review

Hello, I'm planning a 2-week trip with a friend that departs in a couple of days June 15. We just decided to stick to Tokyo and possible day trips from the surrounding area. I am posting here to ask if these day trips are reasonable for us as first-time travelers and any recommendations on splitting or combining day activities. We have an interest in Sightseeing and Anime with me having an additional interest in Military History. 

A couple of questions, are there any places in these planned cities that you would recommend food or activities/sightseeing,

Also are there any war showcase museums like the US Air Force Museum, March Air Field, and USS Iowa Museum In the US that focus on the vehicles/aircraft/Ships used by the military and the history surrounding them. even if I can't visit them during this trip it will be nice to know for when i plan a possible second trip.

Arrive in Tokyo June 15 / depart June 30

Itinerary as of now:

   * The order of when I will do these activities/places is not set and I might move them around 

Day 1: Arrive In Tokyo

• Land at Handea
• Check-in to Hotel (Ryogoku / Sumida area)
• Relax at the Hotel for a bit
• Check out the area around the hotel.

Day 2:  Central Tokyo

• Train to Tokyo Station
  • Pokemon center
  • Imperial Palace
• Walk to Yasukuni-jinja Shrine
  • Yushukan Museum

Day 3: Akihabara

• Train to Akihabara Station 

• Mostly exploring the area and shopping for anime items and some arcade games

• Final Fantasy Cafe

Day 4: Airsoft Day

• Train to Center Kita Station 
  • Play some airsoft at area41 in the evening
• Can/Should I combine this with another day to fill the morning The place opens at 2:00 pm / 14:00

Day 5: Shibuya

• Train to Shibuya station
  • Scramble
  • Shibuya sky
• Train to Harajuku Station
  • Meiji Jingu
  • Yoyogi Park

Day 6: Yokohama 

• Train to Yokohama Station
  • Nissan Global Headquarters Gallery
  • Oga Buga
• Train to Daishibashi Station
  • Round 1 Stadium 

Day 7: Enoshima – Kamakura

• Train to Katase-Enoshima
  • Explore Enoshima Island
    • Enoshima Iwata Cave
  • Attempt to see most of the sightseeing sites (Marked Places on Google Maps)
• Train to Kamakura
  • Kamakura Hiking Trails
  • Visiting shrines

Day 8: Karuizawa

• Train to Karuizawa Station
  • Shiraito Waterfall
  • Onioshidashi Park

Day 9: Matsushima

• Train To Matsushima Station
  • Matsumoto Castle

Day 10: Nikko

• Train to Nikko Station
  • Exploring and seeing the different sights/waterfalls
  • Nothing Exactly planned

Day 11-12: Osaka

• 1st day in Osaka
  • Shinkansen From Tokyo To Osaka (
    • Stopping By to get some fluffy cheesecake
    • Checking into Osaka Hotel
    • Osaka Castle
    • Osaka International Peace Center
• 2nd day in Osaka 
  • Osaka Aquarium
  • Gilion Showroom
  • Return To Tokyo

Days 13/14:

• Still don't have anything planned for these two days