Square Mile Guide: History, Food and Bars in the City of London

The City of London is a strange, wonderful contradiction — a single square mile that’s been continuously occupied since Roman times, now wedged between glass skyscrapers where some of the world’s biggest financial deals happen every day. Wander five minutes in any direction and you’ll pass a Wren church, a Roman wall fragment, a Victorian market hall, and a rooftop bar with views that stretch to the edges of the city, often all on the same street.

We spent a weekend exploring the Square Mile properly — not just cutting through it on the way to somewhere else — and came away convinced it’s one of the most underrated pockets of London for a short, dense trip. Here’s everything worth seeing, eating, and drinking in the City of London.

Must-See Sites in the City of London

Photo: Eluveitie / Wikimedia Commons (CC BY-SA 3.0)

St Paul’s Cathedral

Christopher Wren’s masterpiece has dominated the City’s skyline since 1710, and it’s still one of the most recognisable domes in the world. Climb the 528 steps to the Golden Gallery for a panoramic view over the whole Square Mile, or just sit in the nave for a few minutes — the scale of the place is genuinely humbling.

Don’t miss: the Whispering Gallery, 259 steps up, where the dome’s curved walls carry a whisper from one side to the other — a small architectural party trick that never stops being satisfying.

Tower of London & Tower Bridge

Photo: APK / Wikimedia Commons (CC BY 4.0)

Technically just outside the City’s formal boundary, the Tower of London and Tower Bridge sit close enough that no Square Mile itinerary feels complete without them. Nearly a thousand years of royal history, executions, and the genuinely spectacular Crown Jewels are packed inside the Tower’s walls — budget at least half a day if you want to see it properly rather than rush through.

Our experience: the Yeoman Warder (“Beefeater”) tours are free with admission and worth prioritising — the gallows humour and genuine expertise make the history land in a way the exhibit panels alone don’t.

Leadenhall Market

Photo: Derek Finch / Wikimedia Commons (CC BY-SA 4.0)

This ornate, cobbled Victorian arcade is one of the City’s most photographed corners — cast-iron roofs painted deep green, maroon and cream, with a working market that’s stood on this site since the 14th century. It’s also unmistakably familiar if you’ve seen the Harry Potter films — this was the visual inspiration for Diagon Alley’s entrance.

Other sites worth your time

• The Monument — a 202-foot column marking the site where the Great Fire of London started in 1666, with a viewing platform at the top.
• Bank of England Museum — free entry, and genuinely more interesting than it sounds, including a chance to hold a real gold bar.
• Guildhall — the City’s ceremonial and administrative heart for 800 years, with a medieval Great Hall still used for state occasions.
• Sky Garden — free public viewing gallery at the top of 20 Fenchurch Street (“the Walkie-Talkie”), with the best free view in London if you book ahead.

Best Places to Eat in the City of London

The City’s food scene splits neatly into two: historic pubs serving proper British food, and a genuinely excellent lunch scene built to feed the Square Mile’s office workers — which means some of the best-value, fastest, freshest food in London if you know where to look.

Leadenhall Market

The market itself is packed with small, independent food counters alongside more established restaurants — a good first stop for a coffee, a pastry, or a proper sit-down lunch under the Victorian ironwork.

Smithfield Market area

London’s last surviving wholesale meat market has a genuine early-morning food scene around it — historically, this is where traders and, famously, City workers heading home from a night out would stop for a full English breakfast at dawn. Several excellent traditional British restaurants have grown up around the market itself.

Borough Market (just south, across the river)

Not technically in the City, but close enough (across London Bridge) that it’s worth the ten-minute walk — one of London’s best food markets, with everything from fresh oysters to artisan cheese and street food from around the world.

Don’t miss: the City’s huge concentration of excellent, fast lunch spots on the smaller streets around Bank and Liverpool Street stations — this is genuinely some of the best casual food in London, built for people with a 45-minute lunch break, not tourists, which usually means it’s both cheap and excellent.

Best Bars in the City of London

The City’s bar scene is a real mix of centuries-old pubs and some of London’s most spectacular rooftop bars — a combination you won’t easily find anywhere else in the city.

Historic pubs

• Ye Olde Cheshire Cheese — rebuilt in 1667 after the Great Fire, all dark wood and low ceilings, and a genuine slice of Dickensian London.
• The Blackfriar — an extraordinary Art Nouveau pub built into a wedge-shaped building near Blackfriars station, with gold mosaic friars decorating almost every surface.
• Jamaica Wine House — tucked down a narrow alley, on the site of London’s first coffee house from 1652.

Rooftop and sky bars

• Duck & Waffle — open 24 hours at the top of Heron Tower, with some of the best sunrise and sunset views in the City.
• Sushisamba — three floors up in the Heron Tower, with a striking terrace and skyline views to match the food.
• Coq d’Argent — a rooftop garden bar right above Bank junction, easy to miss from street level and worth seeking out.

Our experience: the free Sky Garden is the best value view in the City by a wide margin, but book your (free) slot well in advance — it fills up fast, especially around sunset.

Where to Stay in the City of London

Staying inside the Square Mile itself puts you within walking distance of almost everything above, and it’s usually quieter at night than the West End since the City empties out once the office workers go home. It’s worth comparing London hotel prices across a few sites before you book — rates vary hugely depending on how close you are to the financial district versus the West End.

Practical Tips for Visiting the City of London

• Getting there: the City is served by several Underground and rail stations — Bank, St Paul’s, Liverpool Street, and Moorgate all sit inside or right on the boundary.
• Best time to visit: weekdays for the full “working City” atmosphere and busiest lunch scene; weekends are quieter and more atmospheric for sightseeing, but many lunch spots close.
• Sky Garden: entry is free but requires advance online booking — slots can fill up more than a week ahead in summer.
• Tower of London tickets: book online in advance for a lower price and to skip the queue, especially in peak season.

Final Thoughts

The City of London rewards slowing down — most visitors either rush through it between bigger sights or skip it entirely for more obviously “London” neighbourhoods, but the mix of deep history, genuinely great food, and some of the best rooftop views in the city make it worth a dedicated day or two of its own.

Where next? Continue exploring England’s coastline with our Eastbourne travel guide, or head further along the south coast to our Bournemouth guide for Durdle Door and the Jurassic Coast.