I would recommend getting a JR Green rail pass if you plan on moving around (like a tourist). It's more expensive than a regular JR pass, but (IMO), it's worth every yen. I don't go to Japan without buying a JR pass. It gives your access to the bullet train reserved cars (rather than the regular cars were it's packed with people and you may end up standing). The seats are wider and the train cars are much less crowded. YOU HAVE TO BUY IT BEFORE ARRIVING IN JAPAN. YOU CANNOT BUY THEM IN JAPAN.
JTB USA | Authorized Japan Rail Pass distributor in United States
JTB USA is the official Japan Rail Pass distributor in the US. Japan Rail Pass allows unlimited rides, including Shinkansen.
I would also recommend getting either a sim card for your phone at the airport (probably Narita), or getting a pocket wifi device for cheap at the airport. It's a super convenient thing to have in Japan.
Another note: Cash is king. You might want to get a cash card (search for Suica and Pasmo) that can be used to pay for most things, from train tickets to 7-11 convenience stores, to vending machines. They don't use credit cards much, except for at hotels where they're accustomed to foreigners using cards. https://www.jreast.co.jp/multi/en/suica/
Try to dress up. Americans are notoriously sloppy/slovenly. Japanese pay A LOT of attention to how a person is dressed. I'm not saying Sunday best, but it's nice to look nice.
Take into account the rainy season.
Americans don't realize how loud they talk. Try to fit in. Don't talk on your phone in busses, on trains or generally in public areas. It's rare to hear a phone ring. They have their phones set on "manner mode" (vibrate only). It's considered rude / crass to talk loudly on the train, or have your phone ring. The only Asians you see doing that are typically from China or Southeast Asia.
When we travel to Japan, we approached it by using a hub/spoke approach. We typically use Tokyo as one hub from which we'd take day trips then return at night, and Kyoto was the other hub. Hiroshima is a full day trip from Kyoto. It sucks to constantly be packing up and moving everything each day. I recommend staying at an AirBnB or local inn if possible. Try to avoid the big touristy hotels, as it isolates you from experiencing the culture.
We listed a bunch of things we'd like to do or see from each hub (Tokyo or Kyoto), then voted on how interested we were in each item. That's how we decided what to do. For instance:
Here's a sample of our itinerary. You need to decide whether to stay in Tokyo first or Kyoto first. We tried to keep the evenings open - to allow some flexibility to rest or change out an attraction.
We wanted to climb Mt. Fuji again, so I wanted to know the moon rise/sun setting times (wanted to hike by a full moon)
The mountain is steep. You can see where you're going right as you get off the bus:
Watch out for altitude sickness:
There are stops with bathroom ($2 donation) and stores for food, shelter, and even beds.
When you get to Kyoto, be sure to go shopping in the gaiten centers... and get a squid-on-a-stick.
If you kids are into electronics, manga or games, they'll like "electric street" (Akihabara) where they can shop in every building, on every floor:
Here's a cost estimator (at the time) to travel if you don't buy a JR rail pass:
Your boy might like seeing the nightlife in Shibuya. It's where youth hang out and have fun. Good people watching. It's also where the busiest crosswalk in the world is located (along with the statue to the dog Hachiko - which is a popular place to meet up with friends). That said, you might want to avoid Kabukicho at night. It's the red light district that they like to take advantage of foreigners and target them. It's okay during the day. https://www.youtube.com/watch?si=Fx6rpkRMSAhdSUoP&v=OCebcZFl9BM&feature=youtu.be
Avoid rush hour on the trains. You'll get pushed, but no one gets mad...it's just part of life in the largest metro area in the world (38-40 million people).