Day 1 (10/19): Tokyo
Arrival day. As you will be arriving at 5:20PM, we have left this day as it is.
Day 2 (10/20): Tokyo
I like for people to get an idea of just how massive Tokyo is when they arrive. The best way to do this is to visit Sky Tree. It gives you a view of the entire city that can't be experienced anywhere else. The area also has one of the most historically significant temples in the entire city, which is surrounded by really nice restaurants, and a lot of shops that do traditional Japanese sweets.
Activities:
- Tokyo Sky Tree
- Sensouji Temple
Day 3 (10/21): Mt. Fuji
Your itinerary had a day in Mt. Fuji, but I wasn't exactly sure if you had something planned for that day, or if you were looking for suggestions for that period of your visit. Mt. Fuji won't be open for climbing to non-professional climbers during your visit. There are many things that are nice to experience in the area, however. I typically send guests to the Lake Kawaguchi area, as it is one of the most accessible spots from Tokyo, and it has a good amount of things to do in that area. There is a really cool theme park, and one of my favorite things to do in the area is visiting a small village where each house has a different activity/traditional craft that you can experience. One of the things that you'll need to be aware of when visiting is that getting to/from each place is quite tough without a car, so you'll need to plan properly, and ahead of time for this particular leg of your trip if you plan on using the buses. I'd like to speak with you again about this part of the trip, but I would suggest the following:
Activities:
- Iyashi no Sato
- Chureito Pagoda
Day 4 (10/22): Tokyo
(left free)
Day 5 - 7 (10/23 - 10/25): Kyoto
I've suggested the place that I've suggested (Gojo Annex), as noted in the planner's notes section, because they will give you an idea of what kind of seasonal activities are happening while you're there, but also because of its location.
The major thing to be aware of when traveling here is to be careful of getting "temple'd" out. The area is the temple/shrine capital of the country and so it's easy to get overwhelmed. I think most people are kind of tired of looking at temples by the 4th or 5th visit. Thus all of my recommendations for this leg of your trip will be centered around things that are not temple or shrine related.
Suggested Activities:
- Sagano Train
- Hozugawa Kudari river boat ride
- Arashiyama area exploration
- Mt. Iwatayama short hike (this is the 'monkey' mountain)
- Bamboo grove behind Tenryu-ji temple
- Pontocho Alleyway (great for restaurants)
- Dinner over the river at Kibunesou
- Gekkeikan Sake museum
Planner's notes: I think that if you are planning on having a night where you enjoy at least one really good meal while traveling here, then Kyoto is going to be a great place to do it. There are a lot of really good restaurants here. The area that I've suggested is just north of Kyoto, and there are restaurants there, where the seats are on top of a river. It's lovely.
Day 8 - 9 (10/26 10/27): Osaka
For Osaka, I wasn't sure if you were planning on going to Universal Studios, and so I don't want to over-plan this section either. I suggest eating as much as you can while there. Maybe catching a baseball game. Whatever you do, you absolutely must visit the Dotonbori area at night. Osaka people are... different.
Day 10 (10/28): Himeiji
Visiting Himeiji Castle is pretty self-explanatory. I highly suggest having a guide for this day. There may be guides that you can find there at the castle that are willing to take you around the castle for free, but it may be advantageous to plan for having a guide beforehand. There are other smaller snack shops, and souvenir places near the castle, but nothing major. Going to Himeiji is typically a day that is set aside specifically for the castle, so I would not suggest planning an evening activity there.
Activity:
- Himeiji Castle
Day 11 (10/29): Osaka
(left free)
Day 12 - 17 (10/30 - 11/04): Tokyo
For your last leg of your trip, I have the following suggestions for activities to spread amongst those days:
Activities:
- Toyosu Fish Market
- Miraikan Emerging Sciences "Museum"
- TeamLab Planets
- Samurai Museum (located in Shinjuku)
- Golden Gai (also Shinjuku)
- JSS Sake taste testing center
- Day trip to Nikko (will take a whole day)
The day trip to Nikko is probably the most important on the list. It is a shrine, but I think that you will appreciate it more having visited all of the other shrines and temples in Kyoto, as it is so very different from them. I've listed these in order in a way. The fish market, MIRAIKAN, and TeamLab Planets are all located within the same vicinity and could make a single day trip if it is something that you wanted to do all at once. The same goes for the Samurai Museum and Golden Gai, they are literally walking distance from each other. The JSS Sake tasting center is an excellent visit if you are into Japanese spirits, but you may need a cab home depending on how much you drink.