Hi, I lived in Japan eight years, including a year in Osaka (near Kyoto). I’ve hosted several American friends and shown them the place. Here is my advice.
**Most important advice first:**In Kyoto, go to Nijojo.. It is one of the few truly impressive tourist attractions in Japan, but it will make your trip worth it. An aboslute must!
OK, let’s look globally at your itinerary. I think I can save you money while greatly increasing the efficiency of your trip. Global advice:
*One week in Tokyo. Then one week in Kyoto/Osaka/Nara. Note that the latter three cities are close together and easily accessible by local trains. In these four cities you can cover 90% of the good tourist spots while getting the best of east and west (two distinct regions in Japan).
*Blow off Hiroshima. It is out of the way and there is not much to see there (admission: I’ve never been there). For the same reason, blow off Nagoya, which really only has the castle (a rather underwhelming reconstruction). I’m not saying that these cities aren’t cool, just that they aren’t great tourist destinations and will suck time away from better stuff.
*Blow off the Japan rail pass. The application process is inconvenient BS, and it is not a great deal unless you are going to wander all over Japan by train, wasting lots of time inside a rail car. Traveling by Shinkansen is not very romantic. The trip between Tokyo and Kyoto is about 2:15, and it is a ripping pain to drag luggage to Tokyo station and lug it onto the train. You will find Haneda airport more user friendly and you will arrive in Osaka in about an hour.
Tokyo is worth a week, especially since you’ll have jet lag and will likely waste a day. Here is what I’d recommend.
Arrive at Narita airport, which is out in the sticks. Do NOT take express trains into Tokyo, take the bus directly to where your hotel is. You should stay in Hibiya or Giza (both close to each other). How about the Imperial in Hibiya? It is top class. This area of Tokyo is very safe and is also active at night, letting you get the most of your time.
Spend your first day/night close to the hotel. See the Hibiya Garden and do some excellent people watching in Ginza, Tokyo’s toniest shopping district. Note, because you are staying at a hotel in this area, you can leisurely spend time here at night.
Asakusa. This has Tokyo’s most impressive temple, lots of good, old-fashioned restaurants, and a cheesy but interesting shopping area (nakamise).
Harajuku, Shibuya, and Shinjuku. This is good especially if this is a Friday or Saturday. These three places (close to each other), are gathering place of Tokyo’s youth. Interesting shopping and people-watching. In Shinjuku, go to Tocho, the capitol of the metropolitan government. It is one of Tokyo’s tallest buildings, and the observation deck is free.
Takao Mountain. Tokyo ain’t just city. This easily climbable mountain is in the eastern part of the metropolis, out in the sticks. It’s beautiful, fun, and great exercise. You’ll be up for it by day 4, and you’ll see Tokyo in a whole new light.
Tsukiji, Akihabara, Ueno. Tsukiji is a good recommendation from Huerta88. Go early and see the fish market in action. Look at all the crazy vendor stalls. There is also a tremendous Buddhist temple near the station that welcomes tourists. Then go to Akihabara and see all the weird electronics stores and stuff they have there. You can walk from there to Ueno, which has one of Tokyo’s biggest parks and more interesting shopping. In your meanderings in this area, you will also see the poverty of the city: many homeless people and scuzzy areas. In general, however, it is not too dangerous. Try to get to Takenoko restaurant in Akihabara, located in Taito-ku 1-choume. It’s in the back streets and offers a chicken-katsu dinner that is to die for. No tourist knows this place!
Sakuragicho, Yokohama. Yokohama is right next to Tokyo, and Sakuragicho is one of my favorite places. At 75 stories, Landmark Tower is one of Asia’s tallest buildings and features a great mall, too. The French restaurant high up on top offers a majestic view of the city and has served me some of the best food I’ve ever had (warning: expensive as hell but worth it!). Your eyes will guide you elsewhere. There is an amusement park with a Ferris wheel, and beyond that is World Porters, another great mall.
Time to go to Osaka. If you have time, wander around Ginza some more. It doesn’t get old very easily. Now get your stuff and go to Haneda. You could even take a taxi if traffic is light. Fly to Osaka. Your hotel should be in Umeda area. This is pretty much the Ginza of Osaka. Good wandering is possible.
Osaka Castle. It’s a reconstruction (and I’ve never been inside the keep proper, to be frank), but the grounds alone are fantastic and hint at what midaevil Japan was like. Go to Shinsaibashi–this is the Shinjuku of Osaka. Then back to Umeda for nighttime fun.
In the morning go to Kyoto and check into your hotel. Let’s make today random temple and attraction day. Frankly, I was never impressed by anything there except Nijyojo, but if you’re going to Japan, you’ve got to do it. Kinkkakuji is a must, and there’s one temple that’s really high up and–oh, I forget the name. All of these places aren’t really active temples anymore; they charge admission. I’m rather cynical.
Now here is some important general advice about Kyoto. The trains suck, and it’s mostly buses. Prepare to walk a lot. The good news is that wandering around Kyoto rewards you. More than the temples, I always enjoyed more the antique stores and various doodads around the city. To me, that’s the real Kyoto. In fact, unless you go out of your way to visit them, you don’t notice the temples all that much.
Here is a culinary tip. Go to Ponta-cho; it’s famous and people will know how to get you there. It’s one narrow street, so you’ll definitely be able to find a restaurant called Shin-Genji. Ask for it if you have to. Get the highest-priced course (last time I checked, ¥5,500 yen). There, you’ve just had the ultimate Japanese meal (with sashimi, fish, tempura, chawanmushi, the works) for a very reasonable price. A must! Sometimes the whole place is rented out for a party. Don’t be discouraged, go back, go back!
Nijyjo. Everything else is secondary.
I would make this random wandering around Kyoto day.
Nara. I only went there on business, but everyone says it’s worth a day, so I believe them.
Your choice. There’s Kobe, or more Nara or more Kyoto. I have less advice to offer about these cities because I only lived in that area for a year. You may find Kyoto totally thrilling and want to spend extra time there. You could spend a week just doing different restaurants in Osaka or Kyoto. I do NOT want to give the impression here that there is enough slack to support a trip to Hiroshima or Nagoya. I think that would kill the pace of your trip.
The return home! Now, you could fly from Kansai Int’l back to Narita (note: there are very few flights in a day; plan carefully). But a better way would just be to fly out of Kansai. It is a very nice airport and not very crowded. If you can’t fly in to Narita and then out of Kansai, it might even be better to fly into Kansai in the first place and then fly to Haneda from there to start your trip. The reason is that Narita is waaaay out in the boonies, whereas both Kansai and Haneda are fairly close to where you want to be.
Note that the respective int’l airports are separate from the local airports. If you fly into Narita, you’ll have to go into the city and then later use Haneda to fly to the local Osaka airport (both of which are nice and convenient; Kyoto does not have its own airport). If you fly into Kansai Int’l (slightly out of the way, but nowhere near as bad as Narita), you’ll later use the local Osaka airport to fly to Haneda.
I think the flight options, as complicated as they sound, are much better than travel by Shinkansen. If you really want to see what the Shinkansen is like, there’s an easy and cheap way to try it: Take it from Osaka to Kyoto. The trip takes about 15 minutes and is one of the cheapest Shinkansen tickets you can buy. Note: The local train (Hankyu) will get you from Osaka to Kyoto in about 45 min. and at a cost of less than $5.
If you follow the above advice, I think you will have a truly kickass trip that shows a lot of really neat stuff. Happy travels, and please let us know how things turn out for you!