I just came back from Tokyo, and man is that place ever a watch lover's dream. Not only do you see really tasteful watches on the wrists of people in the metro, there's an abundance of great watch stores everywhere. If you're ever in Tokyo and want to spend your kids college fund, go to Nakano Broadway for an afternoon. The amount of stock and options are staggering. While I wouldn't say you get killer deals, just being able to see everything in person makes a huge difference.
I went to Tokyo hoping that I may pick up a JDM Seiko, or perhaps even a Grand Seiko, but funnily enough I ended up impulse buying a vintage 1978 Rolex Oysterdate 6694 with a nice silver dial. I know most people are into the Subs and Daytonas (and I mean I am too), but there's just something I've always loved about these cleaner Oysters with stick markers, smooth bezels, and warm silver dials.
It's my first significant watch purchase since I bought my Speedy a decade+ ago. Of course after seeing so many cool watches in person, especially on the vintage side, I now have about 10 other things I want to get.