• Mayfair - This segment of the tour highlights the youthful, ambitious, war hero and bachelor Winston Churchill, eager to make his mark on the world.

Participants will visit his bachelor residence, the home he established with his wife Clementine, and some of his favorite tailors.

There will also be an opportunity to pose with Churchill and Roosevelt at the Allies Statue.

• Henry Poole & Co - This historic Saville Row tailor has a long-standing connection with the Churchill family. They crafted suits for Winston’s father Randolph, and many for Winston throughout his life. (They created the iconic pinstripe suit seen in the Tommy Gun photo of Churchill.) It is said that Winston Churchill still owes the company some money, and the tailors would often find cigar stubs in the pockets when suits were brought in for alterations.

Recently, Henry Poole and Co were commissioned to make Gary Oldman’s suits for the movie “The Darkest Hour.”

• Jermyn Street - “I am a man of simple tastes; I am easily satisfied with the best.” - Winston Churchill.

This exclusive shopping area in St James primarily caters to discerning gentlemen with deep pockets. This is where James Bond purchases his clothes and cologne! Visitors will see many of the shops Sir Winston Churchill frequented, including those selling his preferred aftershaves, and even his favorite cheese monger.

• 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.

• Lock & Co. Hatters - This St James hatter has been crafting hats since 1676. They are the world’s oldest hat shop. Over the years, they have made hats for some of the most famous (and infamous) people in history.

Sir Winston Churchill adopted Lock & Co’s Cambridge and Homburg hats as his trademarks, along with his cigar.

• James J. Fox & Robert Lewis - Sir Winston was rarely seen without his trademark cigar. His favorite brand was Romeo Y Julieta. On this tour, participants will visit the cigar merchant where he purchased his cigars, sit in his chair, and even sample a cigar in the upstairs lounge!
• 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. The tour will start at Spencer House and the smaller house next door where a young Winston grew up. There will be discussions about his great ancestors and his relationship to Diana Spencer (Princess Diana).
• 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 the life of Winston Churchill.
• Houses of Parliament - 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.

• Churchill War Rooms - The tour includes full entry to the Churchill War Rooms, the secret underground headquarters of the British Government during WW2.

In May 1940, Winston Churchill entered the meeting room and declared, “This is the room from which I’ll direct the war.”

Everything in this underground complex is original. The maps, charts, stationery, telephones, and even the ashtrays are as they were left in 1945 when the War Rooms were locked up and left, making this one of Britain’s most important WW2 sites.

The former administration wing of the War Rooms now houses a vast museum dedicated to the life and legacy of Sir Winston Churchill. Visitors will be able to follow his life and career and see many of his personal belongings.

As a private guide, the operator will escort participants into the War Rooms with skip-the-line access and provide an introduction to the site, along with advice on getting the most out of the visit, before leaving them to enjoy this historic site at their leisure.

• Entry to Churchill War Rooms Included

Explore the life of Winston Churchill with a private tour that takes you through the significant and personal locations he cherished, featuring skip-the-line access to The Churchill War Rooms.

Discover his life, career, style, and passions as you wander through the streets, shops, and buildings that held special meaning for him. Begin at his childhood home and those of his esteemed ancestors, then proceed to the residences from his bachelor days and early married life.

“I am a man of simple tastes; I am easily satisfied with the best” - Visit the tailor shops where Winston Churchill had his suits and hats crafted, including the renowned ‘Siren Suits’.

Churchill’s iconic cigar was rarely absent from his lips. Visit his Cigar Merchant and relax in the great man’s chair. (Feel free to enjoy a cigar as well.)

The second part of the tour highlights Churchill’s career, featuring The Houses of Parliament, 10 Downing Street, and, of course, entry to the Churchill War Rooms.

Enjoy a fully private guided tour customized for you.

For a full refund, cancel at least 24 hours before the scheduled departure time.