Afternoon: Omotesandō or Nakameguro
Omotesandō is the easier of the two to spend an afternoon in without a plan. Nakameguro is quieter and better if you would rather walk and talk than browse — it is the one to choose when the point is the conversation.
Ginza and Shibuya are the other two we use, and they pull in opposite directions: Ginza for a composed evening, Shibuya when you want the city loud.
Dinner starts early
Between 6:30 and 8pm is the norm, which surprises visitors arriving from Europe. Punctuality matters more here than almost anywhere — arriving fifteen minutes late is not absorbed the way it is elsewhere.
Tokyo dresses neatly. Understated and well put together reads better than anything showy, and that is true across almost every venue worth booking.
The last train decides the evening
Trains stop around midnight and do not resume until roughly 5am. There is no gentle middle option: either the evening finishes before the last train, or it continues by taxi, which is straightforward but not cheap.
This is worth settling when you book rather than at 11:40pm. Both versions work — they are just different evenings, and the choice is easier made early.
When to come
Cherry blossom season in late March and early April, and the autumn colour from late October into November, are the two peaks. Both are short and both book out well ahead.
Outside those windows Tokyo is easier to arrange at shorter notice, and the city is no less good for it.
Frequently asked questions
What if we are out past the last train?
Decide in advance. Trains stop around midnight, so either the evening finishes before then or it continues by taxi — straightforward, but not cheap.
Do companions in Tokyo speak English?
Yes, and Japanese where you would like the evening conducted in it — useful if you are visiting and would rather not navigate bookings yourself.
When is Tokyo hardest to book?
Cherry blossom in late March and early April, and the autumn colour from late October into November. Both are short and fill early.