Private Sir Winston Churchill Walking Tour of London

Bolton Street was home to Churchill's first 'bachelor pad' which, upon his marriage to Clementine became their first family home. Known for having toy soldier's loitering around the place, a library stocked with £6,000 worth of books and a bedroom which was decorated in his mother's taste, Churchill's home life started here. Whilst still in private ownership, the exterior views of Churchill's old home gives us the chance to discuss Churchill as a young man, as a new husband, and his relationship with his mother and his wife, both of which could be difficult yet loving.

Churchill's marriage to his wife Clementine has often been seen as loving, stable, and faithful. However recent tapes unearthed at Churchill College Cambridge shed some doubt onto this view of their relationship. Was Winston having an affair with the woman dubbed 'The Mistress of Mayfair'? Did she, as some suspect, have plans to blackmail Churchill during the country's darkest hour? Uncover all, including the rumours and gossip that surrounded Churchill and his mistress, outside the address where she lived and where Churchill regularly met her.

This iconic statue of the two great wartime leaders was designed to capture their intimate friendship. Sat on a bench and chatting happily this statue was unveiled by Princess Margaret in 1995 to celebrate the 50th anniversary of the end of the Second World War. Now a popular tourist attraction, this is the perfect place to stop, take a photo, and chat about the great men, their friendship, their differences, and some of outrageous stories that surround them both.

Savile Row is a world-renowned street located in the Mayfair district of London, England. It is widely recognized as the epitome of bespoke tailoring and is considered the spiritual home of traditional British men's clothing.

The street has a long and distinguished history dating back to the 18th century when it first gained prominence as a destination for fashionable attire. Over time, Savile Row became synonymous with exquisite craftsmanship, attention to detail, and the highest standards of tailoring.

Known for his love of the finer things in life, Sir Winston shopped at many of these outstanding boutiques throughout the course of his life. Whilst at Savile Row, your guide will explain which shops supplied what items of clothing to Sir Winston and why many shoppers still flock to these stores, thanks to the connection to the Churchill family.

Sir Winston Churchill had a notable connection to the Royal Academy of Arts in London. While primarily known for his political career and leadership during World War II, Churchill had a keen interest in art and was an accomplished amateur painter.

Churchill's interest in painting led to a close association with the Royal Academy. He exhibited his works at the academy's Summer Exhibition under the pseudonym David Winters, and his lifelong passion for painting and his dedication to the arts is widely acknowledged even today.

In recognition of Churchill's contributions to the arts and his association with the Royal Academy in 1948, he was made an honorary academician, a distinguished title that further solidified his connection to the institution.

Whilst at the Royal Academy of Arts, your guide will explain why painting became so important in Sir Winston’s life, how his paintings give us insight into his life, and why his paintings can be so controversial.

We will walk down the prestigious Burling Arcade (if open) and discuss the role of the jewellers Hancocks in the creation of the Victoria Cross. We will also discuss the 181 recipients of the VC during the Second World War, including Captain Charles Upham the only man during the war to receive the highest medal for 'valour in the presence of the enemy' twice!

Hatchards is one of the oldest and most famous bookstores in London, England. Hatchards has a rich history that dates back over two centuries, is a popular destination for literary enthusiasts. This stunning store has reputation for its extensive collection of books and its commitment to quality and excellence in literature. Throughout its long history, Hatchards has catered to the tastes and interests of a wide range of readers, from the general public to royalty and prominent literary figures, including Sir Winston Churchill, who stocked his considerable personal library with books from this store.

The store has maintained its status as a literary institution and a haven for book lovers, and no stop at Hatchards would be complete without the chance to purchase one of Sir Winston’s publications or a book about the great man by one of the many great literary and academic figures who have written biographies about the greatest Britain who ever lived.

Fortnum & Mason is a renowned luxury department store located in Piccadilly, London. Known for supplying the British royal family, the Churchills were also regular shoppers here. The store's iconic branding and packaging, characterized by the signature Fortnum & Mason hampers, and distinctive, teal-coloured packaging, have become synonymous with luxury and elegance. It was these luxurious hampers that Churchill’s mother sent to Winston whilst fighting in the trenches of the First World War.

Today Fortnum & Mason is an iconic destination for locals and tourists alike, known for its exceptional products, luxurious shopping experience, and a sense of timeless elegance. It remains a symbol of British heritage, showcasing the best of British craftsmanship, gastronomy, and style.

Whilst here, you will have the chance to shop like the Churchill family, or if you prefer, browse the opulent floors of fashion, food, and finery before continuing with your tour.

Here clients can see where Sir Winston purchased his cigars and visit the James J Fox museum (not available on Sundays or Bank Holidays) which contains a selection of artefacts linked to Sir Winston Churchill's smoking habits.

This is also an opportunity to purchase, should you wish, some of the finest cigars in the country.

See one of the finest hatters in the land and learn its links to Sir Winston.

Visit the shop which sells Sir Winston's favourite type of Champagne and, if you wish, purchase a bottle to take home with you. (Not available on Sundays due to the shops opening hours).

Outside Berry Bros & Rudd your guide will also tell you about Sir Winston's infamous drinking habits, including asking for a glass of white wine for breakfast throughout the Second World War whilst the milk for his tea was rationed.

St James's Place is where Churchill's parents lived during his childhood. It is possibly here (although no one can be certain) where Churchill's mother introduced the Prince of Wales, later Edward VII, to his favourite cook Rosa Lewis, who famously chased the young Winston out of her Kitchen with a ladle! Whilst here, you will have the chance to talk about Churchill's father, Lord Randolph Churchill and how Winston's upbringing made him the man that we all recognise today.

As we walk through Green Park your guide will explain how the Royal Parks were used during the Second World War.

Stopping on the Mall you will learn about the relationship between Sir Winston Churchill and his relationships with the monarchy, including Edward VIII, whom he supported during the abduction crisis, George VI who he initially terrified, and Elizabeth II our current reigning monarch.

Whilst outside Buckingham Palace we will also discuss Churchill's plans for the royal family if the invasion of England had taken place, and give you the chance to grab as many photos as you would like.

Learn about how the King and Queen boosted morale during the war and how Churchill's difficult start with King George VI blossomed into one of the closest relationships that a British monarch has shared with a Prime Minister.

Learn about the free-French efforts during the war and why Churchill's orders to destroy the French fleet at Mers-el-Kébir were so important.

Sir Winston was First-Sea-Lord twice, firstly between 1911 and 1915 where he oversaw massive changes to the way the Navy was run. Given Britain's naval might, he ordered that for every ship Germany made, Britain would make two! Finally ousted from the Admiralty in 1915 due to political manoeuvring from the conservatives, Churchill's time at the Admiralty had changed the way war was fought - Churchill's admiralty had developed the world's first Tank!

When Churchill returned to the Admiralty at the outset of the Second World War the British signalled the Royal Navy with the message "Winston is back!" much to the delight of sailors young and old.

As your guide walks you down Whitehall, the home of the British government, your guide will point out the government ministries in which Winston Churchill worked during his illustrious political career.

We will stop outside Downing Street where your guide will explain the key moments of Churchill's two terms as Prime Minister, his role as the leader of the opposition between 1945 and 1951, and how Churchill's shadow still looms large over British politicians today.

Our final stop on Whitehall will be outside the building where Churchill addressed the crowds on VE day, where your guide will explain how the greatest Britain managed to lose the first election after the war.

See one of the many statues of Sir Winston Churchill and learn about his role in the reconstruction of the Houses of Parliament after the Second World War. You will also discover how Churchill was honoured with having his coffin lay in state at Westminster Hall, why his memorial was at St Paul's Cathedral and not Westminster Abbey, and why his statue faces Westminster and not into the Square.

The final location for our tour is Churchill War Rooms.

Originally the underground bunker complex served as the operational headquarters for British Prime Minister Winston Churchill and his government during World War II. Established in 1939 and active throughout the war, the complex provided a secure and secret location for Churchill and his inner circle to manage the British war effort.
Visitors to the Churchill War Rooms can explore the underground complex, walk through the cramped corridors, and see the actual rooms where Churchill and his staff worked and lived.#

A popular tourist attraction and a significant historical site, the War Rooms allows visitors to understand the significance of Churchill’s bunker and the pivotal role it played during World War II.

As tickets to the War Rooms aren’t included in the price of the tour, we recommend that you book tickets in advance for 3 hours after the start time of the tour.