Where Tokyo's trains began, and its workday ends.

This exact spot is where Japan's first railway departed on 14 October 1872, carrying Emperor Meiji on the inaugural 53-minute run to Yokohama. The original station building, designed by American architect Richard Bridgens, burned down in the 1923 Great Kanto earthquake; a faithful reconstruction now stands on the site, housing a small railway history exhibit.

SL Square was built in 1972 to mark the railway's 100th anniversary, its steam locomotive a real C11-292 that ran from 1945 to 1972 and still blows its whistle three times a day. Confusingly, this wasn't originally "Shimbashi" at all — the station here was first called Karasumori, while the original Shimbashi Station (today's Shiodome) became a freight yard in 1914, and the name simply moved down the tracks.

A few steps away, wedged between office towers, sits Karasumori Shrine — founded in 940 after a local warlord reportedly received a vision from a white fox. The area was once pine forest thick with nesting crows, or karasu, which gave the shrine its name. It's easy to walk past without noticing; that's rather the point.

As dusk falls, head into the Shimbashi-Yurakucho underpass — the gado-shita, built beneath one of Japan's oldest elevated rail lines, completed in 1910. Postwar, the low rents under the tracks drew in eateries, and the alley has stayed a salaryman's sanctuary ever since: yakitori smoke, oden steam, and a Showa-era atmosphere that hasn't changed much in seventy years.

The walk ends inside one of these bars, over your first drink and a dish, while your guide shows you how to order, what to say, and how to read the room — the small rituals that make Shimbashi's after-hours world work. What happens next is your Tokyo night.

Pricing note: This is a private tour priced per person, including the first drink and appetiser. Solo travellers: ¥18,000. Groups of 2–6: ¥15,000 per person.