Where to start. I had always wanted to visit Tokyo and Japan, it was so much more than i expected. Tokyo is so huge, a massive sprawling city, oddly built in parts on or around water ways. I expected a concrete jungle , a heaving mass of people moving like ants from place to place, with that big city feel.
I was surprised how small and connected it felt, how friendly the people were, how interested they were in talking to us, and how hospitable the were. Tokyo the large city made small by all the Mom & Pop family run businesses with their small local groups of regular clients.
I feel instantly in love with this city. I was always a lover of Sushi and Japanese food, however i had never really experienced Japan 1st hand.
Clearly the best time and most popular time to visit is in late March early April around the time of the cherry blossom, however it is quite a lot more expensive to visit then, and very hard to get a hotel.
I have visited in both the spring and winter and it's a lot more affordable in the winter, and if you like to ski you can split your trip between Tokyo and Hokkaido in the north and do some skiing which is absolutely a must do, and i will post about this separately. And if you are really motivated there are flights from Hokkaido to Hawaii on Hawaiian Airlines so you can even add a warm beach stop over on the way home.
In Tokyo i like to stay in the Shinjuku District, it's so close to areas with lots of small places to eat and drink and find small bars with live music. A hotel i like is
Keio Plaza Hotel Tokyo
It is in a great location and while it is a large multi story hotel, it is quite comfortable and in the winter the room rate is often sub $190 USD which is 1/2 the price compared to spring, and in Jan/Feb you can find airfares under $750 from SFO.