[ozkai]

Kyoto:

Gion, Pontocho (Night) dinner at a Japanese riverside restaurant on Kiyamaatchi Dori (Street) expect to pay $$$

Finish off the night at a relaxing hostess bar (male only) as they are a great experience.

Nara (Original capital):

Head to the older parts, somewhere like Kashihara City and venture off for a nice walk to the older part of the city as it represents the original Japan street life as it was and still is in that area.

The above two really give you a real original Japan insight.

For shopping and all brands, Osaka, or for real heavy crowds, Tokyo (never been)