Private Sir Winston Churchill Walking Tour Of London

Follow in the footsteps of the greatest Briton who ever lived

Sir Winston Churchill is one of the most iconic figures in British history. In fact, in a 2002 BBC poll, Sir Winston Churchill was voted ‘Britain’s favourite Britain’. Known throughout the world as Britain’s greatest wartime leader, it was Churchill who warned the world of the rise of Nazism and led Britain, her empire, and her allies to victory over the forces of fascism. Churchill was also a devoted husband to his wife Clementine, a beloved father to his children, a controversial politician, an award-winning writer, historian, and a daring soldier. How did Sir Winston manage to accomplish so much?

Remembered fondly by millions, Sir Winston was not without his critics – even during his own lifetime – and today, when we are less prone to hero-worship, some have begun to question Sir Winston’s legacy. Was Winston as faithful to Clementine as some would have us believe? Or was Winston’s link to Lady Castlerose as scandalous as recent research suggests? Did Winston, when he was Home Secretary, order the deployment of troops to quell strikes in the UK’s industrial heartlands? And what about Churchill’s famous ‘Black Dog’ was it depression? Or was it, as some modern mental health experts have suggested, a sign of something else? Find out the answers to these and many more questions on our Private Sir Winston Churchill Walking Tour of London. 

Visit: (the tour includes, but is not limited, to the following locations)

Bolton Street, Bolton Street Churchill’s first ‘bachelor pad’ which, upon his marriage to Clementine became their first family home. Described as having toy soldier’s loitering around the place and a library stocked with £6,000 worth of books, Clementine was shocked when she moved into Bolton Street to discover that her bedroom had been decorated in Winston’s mother’s taste! Whilst still in private ownership, the exterior views of Churchill’s old home give us the chance to discuss Churchill as a young man, including his relationship with his mother and his wife, both of who could be difficult, but adoring.

Berkeley Square, Berkeley Square is the one-time home to Lady Doris Castlerosse the ‘Mistress of Mayfair’. A well-known demi-monde and a scandalous figure, Lady Castlerosse was linked to Jockey’s, Journalists, Actors, Authors, members of the aristocracy and the nouveau riche. Known for her ‘liberal attitude towards sex and her very public affair with her husband’s principal rival Randolph Churchill, she would go on to have 4 portraits painted of her by Sir Winston compared to Clementine’s one. Today, and in the 1930s, rumours claim that Doris Winston’s mistress. But did Winston really stray? And did Doris, as some suspect, have plans to blackmail Churchill and possibly bring down the government during Britain’s darkest hour?

Churchill And Roosevelt Allies Sculpture This statue stands as a monument to the two great wartime leaders, and the special relationship that links Britain and the United States of America. Designed to capture the intimate friendship between Churchill and Roosevelt, the 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 take a photo, and discuss the great men, their friendship, their differences, and some of the outrageous stories that surround them both.

Burlington Arcade, Burling Arcade is one of the finest shopping arcades in London and is full of its own unique shops, characters and history. Outside the world-renowned jewellers ‘Hancocks,’ we will discuss their role in the creation of the Victoria Cross (or the VC as it’s sometimes known) the highest honour for bravery in the face of the enemy. Whilst enjoying the view of some of Hancock’s finery your guide will explain how during the Second World War there were 181 recipients of the VC and will reveal the story of Captain Charles Upham – the only man to receive the VC twice!

James J. Fox & Robert Lewis, when we think of Churchill we always think of his famous cigars, and it is here where Sir Winston (or more accurately Sir Winston’s staff) purchased his cigars. During our time here we will visit the James J Fox museum (not available on Sundays or Bank Holidays) which contains a selection of letters, intimate items, and objects linked to Sir Winston Churchill’s smoking habits. Should you wish to enjoy one, or more, of Sir Winston’s favourite Cuban cigars, then this is also an opportunity to purchase them from the very same shop! Please note that visitors from the USA may purchase and transport 100 Cuban Cigars from the UK back to the United States. Should you wish to take any of your cigars back with you, our guide and the staff at James J Fox can advise you on how to transport them for your return journey.  For more details, please contact us.  

Berry Bros. & Rudd, if you were to try to drink as much as Sir Winston did you wouldn’t have made it this far on the tour! Whilst outside Berry Bros & Rudd your guide will explain all about the business’ unique history, including its tradition of weighing people. Known for supplying royalty (including the current Queen and The Prince of Wales) as well as Prime Ministers, celebrities, and some of the best parties in town, Berry Bros & Rudd is one of the world’s leading wine merchants. Whilst here our guide will reveal details of Sir Winston’s infamous drinking habits, including asking for a glass of white wine for breakfast throughout the Second World War, as well as some of his most memorable alcohol-related one-liners. Should you wish to purchase some of Sir Winston’s favourite drinks, including his favourite type of Champagne then our quick stop at Berry Brother’s & Rudd is highly recommended! (Sadly we are unable to stop here on Sundays due to the shops opening hours) And your guide will be more than willing to help you make a choice of drink which would make Sir Winton proud.

Churchill War Rooms, the final stop on your journey exploring the life of Sir Winston Churchill will be outside the Churchill War Rooms. If you wish to visit the war rooms then we highly recommend you book your tickets in advance for 3 hours after the start time of the tour. If you have not booked tickets, you may be disappointed as queues in peak months can last for several hours! After a quick history of the War Rooms, their importance, and Sir Winston’s role in their creation, even though he was not in government at the time, your guide will depart leaving you to enjoy the rest of your day.

David & Chris
David & Chris
2020-08-24
Thank you Henry for an amazing day out! We took this tour with Henry a few days ago and really enjoyed it. We're sometimes a bit wary of booking a private tour as a Gay couple (you never know what the guide is going to be like) but Henry made us both feel totally at ease. He collected us from our hotel, provided us with face masks and hand sanitizer, and drove us out to the Cotswolds. We were also really lucky that Henry was able to get us into places that are currently closed to the public, thanks to his relationship with the locations that we visited. He was charming, well informed, and funny. Henry was able to tell us lots of interesting facts about the places that we visited, and told us where to stand to get the best photos. Thanks for an amazing day out, will definately book with Tours of the UK again in the future.
Selina E
Selina E
2020-02-16
I spy with my little eye.... We took this tour with Chris in January whilst we were visiting after Christmas. The tour is really informative, full of great facts and stories, and even included some locations from the James Bond franchise. It was great hearing the history of the British Secret Services and their exploits during the Second World War and The Cold War. We also had no idea that Roald Dalh was a spy and had helped write the Bond films. We'll be back for the Bond Tour next time.
Eric D
Eric D
2020-02-16
Great day out with Dewi We took out grandkids on the tour with Dewi and it was fantastic. The grandkids loved every second of tour and the locations that we visited. Highly recommended for any Doctor Who fan
KingBooScaresYou
KingBooScaresYou
2020-01-30
Absolutely fantastic tour! I had the pleasure of going on the Churchill walking tour today with my guide Karl. As an avid history fan I was in my element seeing the famous sites, and Karl really brought them to life. He couldn't have been more friendly, knowledgable and enthusiastic, and evidently has a real passion for history which came across in this tour. I thoroughly recommend Karl and this tour to any fellow history geeks out there! You wont be disappointed! Thanks for an amazing day!!
Karen W
Karen W
2019-12-01
Excellent value Kathryn was a great host very knowledgable about sherlock movies and other movies shot in the area. We went past the sherlock Holmes pub and many more places of interest
Natalie D
Natalie D
2019-11-16
Really fun day out! I went on the Harry Potter tour with Dewi and he was brilliant. Was a really fun tour and so informative. I looooooove Harry Potter and it was so cool learning all the facts and seeing the spots of filming. Would definitely recommend!
Lauren
Lauren
2019-11-15
Absolute riot I went on a hybrid tour with Dewi at the end of the summer and it was such good fun, me and my friend (we’re the folks in the pictures in the header!) got to wander round London being absolute needs and learning about the locations of doctor who and Harry Potter and evening stopping off at some of London’s best drinking establishments. Dewi was very knowledgable and a lot of fun, would recommend in a heartbeat!
Cez1984
Cez1984
2019-11-15
Dewi was a fantastic guide! Brilliant tour around lots of filming sights in London and a chance to recreate famous scenes from the film. Our guide Dewi was really informative and enthusiastic and we had a really good laugh all throughout the whole tour. Highly recommended