Tower of London to St Paul's: An Ancient Square Mile Walking Tour
About the Tour
London's ancient streets hold 2000 years of history just beneath, and above the surface. On this walking tour from the Tower of London to St Paul's, you'll trace the city's layered past through Roman ruins, Great Fire landmarks, and the Georgian financial institutions that made London the world's commercial capital.
The tour starts outside the Tower of London, heading through the medieval lanes and grand main streets of the old city. Along the way, you'll pass the entrance to the Victorian Tower subway, step inside the ruins of St Dunstan in the East – a bombed-out church now open to the sky as a public garden – and follow the riverfront past the Custom House, where Geoffrey Chaucer once worked as controller of customs. You'll wind through narrow alleys lined with centuries-old pubs before arriving at Bank Junction, where the Bank of England, the Royal Exchange, and Mansion House cluster together.
The route takes you through the medieval trading streets of Lombard Street and Birchin Lane, through courtyard alleys that once housed the city's first coffee houses, and along Roman Watling Street toward St Paul's. The tour ends in the small garden beside Admiral Arthur Phillip's statue, with Wren's great Cathedral rising ahead of you.
On this 90-minute tour, you'll have a chance to:
- Explore St Dunstan in the East, a Wren-designed church whose surviving Gothic tower has stood since 1703
- Visit the Monument to the Great Fire of London, whose 212-foot column commemorates the disastrous events of September 1666
- Discover how Lloyd's of London grew from a Lombard Street coffee shop first recorded in 1682 to the global insurance market of today
- Walk through St Michael's Alley to the Jamaica Wine House, built on the site of London's first coffee shop
- Learn how the Billingsgate fish porters' leather hats were modelled on headwear worn at the Battle of Agincourt
- See the London Mithraeum, a Roman temple to Mithras buried seven metres beneath the city's current streets
- Explore some of the buildings at the centre of the City of London as they overlook the Bank junction as shown on the main photo
This tour packs Roman London, medieval merchants, and the architects who rebuilt the city after 1666 into a two-mile walk that rewards anyone curious about what lies behind the city's familiar skyline.
Tour Producer
Martin Hughes
London isn’t just where I live - it’s in my bones. I’ve spent nearly my entire life in South London, and that lifelong connection shapes every step of the tours I lead. For me, this isn’t just the “best city in the world” (though I stand by that wholeheartedly); it’s a living storybook, layered with voices, moments, and histories I’ve grown up hearing, exploring, and sharing.
My ties to London run generations deep. My grandfathers served here during the Blitz - one on anti-aircraft guns, the other as a volunteer fireman - protecting these very streets while carrying on their daily lives. Those family stories sparked a lasting fascination with the human side of history: the lives behind the landmarks, the drama, resilience, and character you simply won’t find on a plaque.
I’ve been working in London since the mid-1990s, guiding people through its most iconic buildings and hidden corners. Years of fantastic feedback led me to create these tours so more people could experience the city the way I know it. Join me, and you’ll get more than facts. What you can expect isn’t just history, but a lively blend of insider knowledge, untold stories, and a good dose of humour. Join me, and I’ll show you a London you won’t find in guidebooks - one that’s personal, surprising, and unforgettable.
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Preview Location
Location 8
Custom House
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The building to your left as you look at the river is the Custom House. In 979 King Ethelred levied the first custom duty and in 1275 the first Custom house building was constructed east of its current location in the Old Wool ... Read More
How VoiceMap Works
Major Landmarks
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All Hallows by the Tower
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St Dunstan in the East Church Garden
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Old Billingsgate
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Church of Saint Magnus-the-Martyr
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Monument to the Great Fire of London
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Bank of England
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The Royal Exchange
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London Mithraeum | Bloomberg SPACE
Getting There
Route Overview
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Start locationLondon EC3N 4AB, UK -
Total distance3km -
Final locationUnnamed Road, London EC4M 5SB, UK -
Distance back to start location1km
Directions to Starting Point
The tour starts outside the Tower of London near the gift shop entrance under the large tree. The closest tube station is Tower Hill and is a short walk from Fenchurch Street main line rail station.
This tour is ideal if you have spent time visiting the Tower of London and want a less direct route to St Paul's Cathedral.
Tips
Places to stop along the way
During the tour we will visit a number of locations where you can pause the tour and visit some of the buildings in more detail most of which are free. These are explained in the tour but include:
All Hallows by the tower
The Monument
The Royal exchange
Underground Roman temple
You will also walk past a couple of my favourite pubs The Ship and the Jamaica Wine House.
Public Toilets can be found on the left after the Tower subway and at Cannon Street Station close to the end of the tour.
Best time of day
This tour is good at all times of the day. Lunchtimes can see some of the locations busy as Londoners seek a quiet spot to have lunch. All of the suggested additional stops are open during office hours. The Views of St Paul's grow as we get closer to the final destination and are especially impressive at night when the Cathedral is lit up.
Precautions
You will need to cross several main roads so please take care and use the crossings where they are available. As with all large cities do be aware of your surroundings and take care with your phone and possessions.
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