Last Minute Free Valentine's Day Idea: Walking Tour of the City of London from Tragedy to Love

For a free (or cheap, if you turn it into a pub crawl) Valentine’s Day in London, we have created a walking tour with a difference. We have called it the Tragedy to Love walking tour and it guides you via historical palaces, memorials, back alleys, hidden plaques, stunning buildings (modern and hundreds of years old) to fragrant gardens perfect for proposals, picnics or just a cuddle. This walk should take you 30-60 minutes.

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Prison, war and executions

Start at Tower Hill tube station. Look upon the Tower of London, think about how beastly the White Tower (which is the centre one that isn’t really white anymore) would have appeared to ships sailing up the Thames. Turn right and walk into Trinity Square Gardens in front of Trinity House. Three points of interest in this garden: the Merchant Navy Memorials which always have poppies, the Tower Hill execution scaffold site of many public executions and the former Port of London Authority (interesting for the statue of the naked man poised with a cute hip swing).

Evil at the end of the road

From the square walk north up Savage Gardens (past DoubleTree by Hilton where you could always stop for a drink at the fantastic rooftop bar with views over the city) until the road becomes a spooky dark small alley underneath the Fenchurch Street rail station. Turn left up Crutched Friars. The 'postmodern gothic' office building you’ll see glooming over you at the end of this road is Minster Court, famed as Cruella De Ville’s HQ, the “House of de Vil”, in the 101 Dalmatians film made in 1996.

A bit of transparency into someone else’s world

Don’t walk too far up Crutched Friars. When you see an archway on your right with vehicle height restrictions, turn right. It’s called French Ordinary Court but, apart from the name, there’s not much that’s romantic about it. The lane leads you by the modern Lloyd's Shipping Register by Richard Rogers. This transparent building is an extension of the original (you’ll see in a moment). It comes alive when office workers walk around the exposed corridors and the lifts travel up and down.

Photo: Katsuhisa Kida

Life would be nothing without a woman or a girl

You’ll reappear on Fenchurch Street next to the East India arms, which is positively buzzing with City professionals before their commute back to Essex in the evening. A quick detour is needed at this point. Briefly turn right and cross the road so you’re opposite the original Lloyd’s Shipping Register which is the most lovely of buildings, decorated with a golden ship weathervane on the roof and carvings of women all holding and protecting vessels. Never take a woman for granted.

Consider change and follow your conscience (by pretending the Gresham Grasshopper is Jiminy Cricket)

Turn back on yourself, walk down Fenchurch Street in the opposite direction. Continue onto Lombard Street where you’ll walk under a hanging Grasshopper, the family crest of Sir Thomas Gresham who lived here. Take the third right up Change Alley highlighted by a huge plaque of an anchor. In this back alley is also a plaque in the shape of another grasshopper to mark the site of Garraways Coffee House which was the first shop in England to serve and sell tea.

Come out of Change Alley onto Cornhill and turn left towards Bank. The treasure hunt of grasshoppers concludes at the Royal Exchange where you need to look up and spot the gold weathervane grasshopper, again placed in honour of the Gresham family. This luxury shopping centre was so loved (or, more realistically, approved) by Queen Elizabeth I that she declared it royal and awarded an alcohol license.

Crossroads of the journey 

Stand still here, in the pulsing, noisy heart of the City of London. For you engaged couples, if you want to see the most secret yet desired wedding venues in the city then walk towards Cannon Street station to see Skinners’ Hall.

If your relationship has matured and grown with your lifestyle, walk down Cheapside to the equestrian-styled Saddlers’ Hall which is hidden down Gutter Lane (don’t be put off by the historic City street names, this was the major trading hub back in the day).

For couples who appreciate historical architecture and art, a stunning, hugely atmospheric venue is Apothecaries Hall at Blackfriars. This venue really knocks the socks off every visitor. Walk down Queen Victoria Street or wander west beside the River Thames.

One direction to love

Despite the options above, the ultimate end to this City Valentine’s Day is in a secluded fragrant garden by the Museum of London, via Love Lane.

Walk up Poultry (with the romantic St Paul’s Cathedral appearing overhead) and turn right up Ironmonger Lane to Guildhall, one of our favourite venues in London. Guildhall Yard has a large black circle outlining where the ancient Roman amphitheatre (think gladiators) once was situated (you can see the foundations by going to the basement of the Guildhall Art Gallery).

Walk to Aldermanbury by Guildhall Library and walk towards St Mary Aldermanbury’s Garden, a lush pocket of green in the City. More importantly, it’s on Love Lane. We wonder how many people have popped the question here but probably there have been more wedding photo shoots. Have a little kiss and a cuddle here. It is only right.

A beautiful thank you letter from a couple who got married at Skinners' Hall with Party Ingredients recently.

End of the tour

Walk to the end of Love Lane, turn right onto Wood Street and enter Barber-Surgeons’ Garden off London Wall. This colourful garden is not only within the remains of the London Wall but was used by the Barber-Surgeons to “present a broad view of the way in which plants have been used from the earliest times to the present day in the practice of medicine and surgery” (City of London). 

Round up your tour by having a picnic here on the lawn.  If the weather is shocking then Plan B is to explore the Museum of London (which you can’t miss from where you’re standing) which should be on your bucket list anyway!