A wine bar crawl is the most underrated night out in London. Everyone talks about the historic pubs, but the city’s old wine bars are quieter, stranger and usually older than they look — and because most of them sit in the City of London and around Fleet Street, you can walk the whole route in an evening.

Here is the self-guided version we give friends. Allow three to four hours, start around 5:30 PM, and go on a weekday.

Start at Fleet Street, while the lawyers are still in

Fleet Street is the right place to begin because it has the densest cluster of old wine bars in London, and because the area empties out early. El Vino, the old journalists’ haunt, is the obvious first stop: women were not allowed to order at the bar there until a court case in 1982, and it inspired Pomeroy’s in Rumpole of the Bailey. The newspapers left decades ago, but the barristers never did, so the bars still fill from about half past five.

Order a flight rather than a bottle at your first stop. Three small pours side by side will tell you more about what you actually like than a whole bottle of one thing, and it keeps you upright for the rest of the night. There is more on this in our guide to wine tasting in London.

Then get off the main road and into the alleys

The good stuff on Fleet Street is never on Fleet Street. Duck into Wine Office Court for Ye Olde Cheshire Cheese, rebuilt in 1667 after the Great Fire and a Dickens haunt. Gough Square, a minute further, has Dr Johnson’s House. St Bride’s, the journalists’ church, is tucked behind the shopfronts, and the Temple Bar dragon marks where the City of London officially begins.

This stretch is the heart of our Fleet Street after dark walk, and it is worth doing slowly. Half of what makes a wine bar crawl good is the five minutes of walking between each one.

Go underground

London drinks wine below street level more than almost any other city, and that is not an accident. Centuries as one of Europe’s great wine-trading ports left the City riddled with cellars and vaults built to hold barrels, and a lot of them are now bars.

Gordon’s on Villiers Street is the one everyone names — usually called London’s oldest wine bar, open since the 1890s, candlelit, and with Kipling having lived in the building upstairs while he wrote The Light That Failed. It is also, fair warning, extremely popular, so go early or go midweek. We have written up several more in London’s oldest wine bars.

Finish high

End the crawl on a rooftop. The City has a cluster of bar terraces with views straight at St Paul’s and down the Thames, and they are at their best in the half hour after sunset, when the dome lights up and the office towers are still catching the last of the sky. Walking from a candlelit cellar up to a rooftop in one evening is the whole point of the route.

Five practical things worth knowing

  • Go on a weekday. The City of London empties at weekends. Many bars shut entirely on Saturday and Sunday, which catches visitors out constantly.
  • Start earlier than you think. Wine bars here fill from about 5:30 PM. By 7 PM the good ones are three deep.
  • Eat something. A cheese board changes how the wine tastes and keeps the evening going.
  • Ask what is open. Many bars use preservation systems, so you can often try a premium bottle by the glass. Ask what was opened that day.
  • Keep it tight. Three or four stops within walking distance beats six spread across town.

Would rather not plan it?

That is more or less what our Secret Wine Bars of London tour is: the same route, done properly, with someone who knows which bars are worth the stop and what to order when you get there. Three hours, six people maximum, 6 PM starts from Fleet Street, £59 for the guiding (wine and food are paid for as you go).

If you would rather drink beer than wine, the same walk works with the City’s historic pubs instead.