My wife and I are poking at the idea as well. We're planning to do Tokyo, Kyoto, Nara (deer park). Random things I've noticed already based on research and chatting with those who have gone recently (Not exhaustive):
- JR National pass should be acquired before you go. I ordered mine online for around $330 per person including delivery and as far as I can tell offers unlimited usage of the JR rail line for a set amount of days. Supposedly they can courier it to you within about 3 business days. You receive a document to exchange at a JR exchange station. Look up the exchange locations to determine how to exchange it. No idea whether there's even cheaper options.
- HOWEVER, JR is 1 of about 5 rail companies. It's not "compatible" with the other rail lines. For the other modes of transportation, consider a Suica or Pasmo. It's a re loadable card used for travel and on occasion paying for small items.
- Taxis are expensive, most people I talk to say don't bother. Unless you're ridiculously rich.
- Although wifi is everywhere, logging in is not easy. Consider looking into a Japan data SIM card or a pocket wifi. The latter is more expensive than the former.
- Download Google translate on your phone and download the Japan language pack. Even offline, you can take a picture with Japanese words, and get a rough translation. Signs, packages, books etc. can be photographed, then you highlight a section you want to know and it will translate.
- Convenience stores are freaking awesome. A few friends who have gone before (me included) don't bat an eye at the idea of dropping a few hundred CAD$ in them. So many delicious things there at prices not horribly different to supermarkets.
- Etiquette is a major culture shocker. You may want to spend a little time looking it up. The major one that I always forget is money exchange. You generally place the money in a tray they provide.
- Many friends say spend more time in Kyoto if you like the old style stuff. Ryokan, onsen and dress up in traditional clothing for a photo shoot are worth looking into, but do come with minor culture shock. If not all out photo shoot, you can rent traditional clothing in Kyoto and wander around the city in that for a few hours. 5/50 Yen coins are considered good luck. Save those for the temples.
- Beds in Japan are really small. Don't chase the best prices, make sure it's a room you can be comfortable in. Many rooms are ok for 1 person and very crowded for 2. Not idea for "honeymoon" activities. Some reviews on some hotels also mention sound proofing that leaves something to be desired.
- There's supposedly a ton of stuff that is super cool, but cannot be purchased by foreigners. Usually, this stuff is technology related.
- Shoes. Lots of walking has been noticed when I eyeball our mock itinerary thus far. Good shoes and good insoles/gel heel slips will go a long way. Consider practical shoes that match outfits prior to going on the trip if needed.
- Always give yourself extra time. Don't plan too many things each day. I'd expect to get lost a few times. If you're early, always cool things like a convenience store or road side things to look at.
- Japan only things. Go look at giant robots, Disney Sea, Ghibli, culture, crazy vending machines, food, pachinko... Just watching people doing their regular day activities is as fascinating as tourist traps on occasion.
- Time management. There's too much to see in Japan to see it all on your trip. Plan accordingly, realize you may have to drop certain items off your itinerary. But it's ok! It just means there's reasons to go back to Japan later on.
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