Your evening starts at JR Oimachi Station, which is just two minutes off the Yamanote (loop) Line from Shinagawa. Within moments we're snaking our way down the bustling, narrow backstreets that give this neighborhood the kind of character you just don't find in Tokyo's large-scale entertainment districts. It won't be long before we duck into our first tachinomi ("standing bar") for a cold beer and some tasty local, Japanese style pub grub. If beer's not your thing, there are other options. Also available, in case you are a little wary of some of the more "advanced" Japanese foods, are more classically Western palate-friendly options.
Hunger staved for the moment, we embark on an educational walk, explaining (with visual aids aplenty) the vagaries of the Japanese nightlife scene. It's a lighthearted stroll, and we have fun with it; you needn't worry about it being raucous or off-color, and this tour is suitable for teens too, should you have them in tow.
It's probably not going to surprise you that nightlife in Japan is not just about bars and clubs. There's something for everyone, seemingly at every stage of life, and every stage of the night. And since it's Japan, it's a totally safe stroll about these remarkably clean streets!
After about 30 minutes of real-world edumacation, we stop by our second spot for some yakitori (grilled chicken skewers) or perhaps some kushikatsu (fried goodies, also on skewers). Or maybe somewhere else. With a maximum of 5 guests, we've got flexibility. Regardless of where we stop, you can count on some impromptu interactions with locals. You may have heard that Tokyo people are not very social with strangers, but there must be something in the air in the places we go tonight. We find this air very refreshing.
Two restaurants and two drinks in, it's time to say goodbye to Oimachi. Fear not, though, because we're just a six minute ride to our next stop, Kamata. We've got a whole new set of sights for you here, and our guides go where most Japanese guides fear to take you (probably they're just afraid you'll be bored, but we feel confident you won't). Kamata has some great bubble era architecture with a smattering of fairly recent spruce-ups, and a classic old skool shotengai ("shopping street"). It's also got some good grub, and we have a spot with a chill vibe and friendly clientele all lined up. This is one of those endangered parts of Tokyo that's a bustling village with a distinct identity. While other parts succumb to chain stores and homogenization, Kamata stands strong, if perhaps not quite as classily.
Before you know it, we've been together for at least three hours, and it's time to really say goodbye. Your guide will be happy to get you to the train station, or even recommend another spot for a drink or two. You're on vacation after all.
Your guide will be a native or honestly equivalent speaker. Language barriers are a drag.