Explore Winston Churchill’s London on a small group walking tour. Visit his childhood home, favorite cigar shop, and the Churchill War Rooms. Learn about Britain’s greatest Prime Minister.
Explore Winston Churchill’s London on a small group walking tour. Visit his childhood home, favorite cigar shop, and the Churchill War Rooms. Learn about Britain’s greatest Prime Minister.
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Mayfair - Explore the most prestigious area of London.
This segment of the tour highlights the young, ambitious, war hero and bachelor Winston Churchill, eager to make his mark on the world.
Visit his first childhood home, bachelor pad, and the residence he established with his wife Clementine, along with a stop at some of his favorite tailors….
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Mayfair - Explore the most prestigious area of London.
This segment of the tour highlights the young, ambitious, war hero and bachelor Winston Churchill, eager to make his mark on the world.
Visit his first childhood home, bachelor pad, and the residence he established with his wife Clementine, along with a stop at some of his favorite tailors.
You’ll also have the opportunity to pose with Churchill and Roosevelt at the Allies Statue.
- Savile Row - The destination for bespoke suits, shirts, or formal wear.
Stop by Henry Poole and Co., a historic Savile Row tailor with a long-standing connection to the Churchill family. They crafted suits for Winston’s father Randolph and many for Winston himself throughout his life, including the famous pinstripe suit in the Tommy Gun photo of Churchill. It’s said that Winston Churchill still owes the company some money, and the tailors often found cigar stubs in the pockets when suits came in for alterations.
Recently, Henry Poole and Co. were commissioned to make Gary Oldman’s suits for the movie “The Darkest Hour.”
- St. James’s - “I am a man of simple tastes; I am easily satisfied with the best.” - Winston Churchill.
This exclusive shopping area in St. James caters mainly to discerning gentlemen with deep pockets. This is where James Bond buys his clothes and cologne! You’ll see many of the shops Sir Winston Churchill frequented, including those selling his preferred aftershaves and even his favorite cheesemonger.
- Spencer House - Winston Churchill was born at Blenheim Palace in 1874, but his early years were spent in London. His father, Lord Randolph Churchill, was the son of the 7th Duke of Marlborough, with the family name being Spencer-Churchill. We will start at Spencer House and the smaller house next door where a young Winston grew up. We will discuss his great ancestors and his relationship to Diana Spencer (Princess Diana).
- Turnbull & Asser - Churchill was a stylish dresser, but sometimes he needed something practical yet comfortable when out on the grounds of his country estate, Chartwell, or during the cold nights watching the bombs fall over London. Enter the ‘Romper Suit’ or ‘Siren Suit’ as it became known. Churchill trusted only one company to make these to his specifications, his shirt maker Turnbull & Asser.
This company was also the first to receive a Royal Warrant from Prince Charles.
- James J. Fox & Robert Lewis - Sir Winston was rarely seen without his trademark cigar. His favorite brand was Romeo Y Julieta. On this tour, you’ll visit the cigar merchant where he purchased his cigars, sit in his chair, and even sample a cigar in the upstairs lounge!
- Saint Margaret’s Church on Parliament Square - On 12th September 1908, Winston Churchill married Clementine Hozier at this church right next to Westminster Abbey. Known as the Parish Church of the House of Commons, it was a regular place of celebration, memorial, or thanksgiving during Winston Churchill’s life.
- Parliament Square - Across the road from the Houses of Parliament, the statue of Sir Winston Churchill gazes at his beloved House of Commons.
Churchill was offered a peerage and a dukedom but declined both as this would prevent him or his male descendants from serving in the house. Let’s pause here for a while and discuss the political life and anecdotes of this extraordinary man.
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Whitehall - A brief look at a pub with a connection to all British Prime Ministers, The Red Lion.
It’s no secret that Churchill loved a drink, and he also cherished tradition.
This pub has served every Prime Minister a drink, including Winston Churchill. He certainly wasn’t going to break that tradition!
- Downing Street - The official residence of the Prime Minister since Robert Walpole.
This famous little street is known worldwide. The door that Winston Churchill walked through as Prime Minister in 1940 is preserved and on display in the Churchill War Rooms.
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Churchill War Rooms - The tour concludes at the Cabinet War Rooms and Churchill Museum.
Your guide will provide details of this once top-secret bunker from which Winston Churchill directed the British side of WWII.
These secret map rooms are now open to the public, but it is strongly advised to book in advance if you plan to visit.

- Expert guides lead the way.
- Discover the city’s history and culture.
- Visit iconic landmarks and hidden gems.
- Includes entrance fees to major attractions.
- Comfortable transportation throughout the tour.
- Plenty of photo opportunities.
- Insider tips and recommendations from your guide.
- Interactive and engaging experience.
- Small group sizes…
- Expert guides lead the way.
- Discover the city’s history and culture.
- Visit iconic landmarks and hidden gems.
- Includes entrance fees to major attractions.
- Comfortable transportation throughout the tour.
- Plenty of photo opportunities.
- Insider tips and recommendations from your guide.
- Interactive and engaging experience.
- Small group sizes for a personalized experience.
- Souvenir shop visits included.
- Entry to Churchill War Rooms
- Entry to Churchill War Rooms
Explore Winston Churchill’s life on this intimate, history-themed tour. Choose from various convenient tour times and embark with only your guide for company. Discover where Churchill lived during his childhood and youth, find out where he bought his suits, and visit his favorite cigar shop. Then, see the church where he was married, admire 10 Downing…
Explore Winston Churchill’s life on this intimate, history-themed tour. Choose from various convenient tour times and embark with only your guide for company. Discover where Churchill lived during his childhood and youth, find out where he bought his suits, and visit his favorite cigar shop. Then, see the church where he was married, admire 10 Downing Street and the Houses of Parliament. Conclude at the Churchill War Rooms, where your guide will share its captivating history.
After the tour, you have the option to visit the Churchill War Rooms, using the knowledge gained to enrich your experience.
The private version of this tour has received 100% Five Star Reviews and is now available in this new smaller group format, allowing more travelers to learn about Britain’s greatest Prime Minister.
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.