Sir Winston Churchill Tour of England

What to expect on this itinerary
Perhaps no statesman has defined the last century more than Sir Winston Churchill, the hero who stitched a nation together during its most trying times. This unique tour of England commemorates and celebrates the legend, taking you on an evocative journey through his entire life and legacy. You'll explore legendary command posts and bunkers as well as his lesser-seen private life and tastes. From palaces to tunnels, art collections to stylish Churchill bars, this is a journey following in the footsteps of a legend and a nation.
Customizable Itinerary
London – Stylish Welcomes at the Churchill Bar & Terrace
Winston Churchill had style. Not quite the same style as Queen Elizabeth or the monarchs, but an equally compelling flair that offers an insight into iconic England. You'll be greeted at the airport and transferred to your five-star luxury accommodation. Freshen up and start the immersion at the Churchill Bar & Terrace, carefully designed to reflect the statesman's taste in photography, art, and travel. Churchill Craft Gin is the base of many of their signature cocktails while a selection of cigars enables the guide to touch on the former prime minister's personal tastes. Providing the backdrop is a life-sized bronze of Churchill in conversation with Franklin Roosevelt, another talking point as you're introduced to the tour by your expert local guide. The evening is at your leisure.
What's Included:
London – Historic Harrow School and Seven Prime Ministers
London – Day Trip to Oxfordshire – Private Tour of Blenheim Palace and Churchill's Resting Place
Kent – Exploring Churchill's Family Home
Dover – Incredible WWII Tunnels and Evocative War History
London – Churchill's Remarkable Cabinet War Rooms
London – WWII Operations Bunker and Legendary Aircraft
London – Departure
Trip Highlights
- Fully explore the history of Winston Churchill, taking a journey from his ancestral home, through his younger years, and then his defining moments in World War II
- Enjoy a private tour of the exquisite Blenheim Palace, home to the Spencer-Churchill family and arguably the finest stately home in the country
- Wander through WWII tunnels and discover the command rooms that defined history
- Discover the tastes and styles of Churchill with visits to his family home and exhibitions of his private art collections
- Evoke the engineering masterpieces of Churchill's time with visits to see code-cracking machines and hundreds of historic aircraft
- Stay in Churchill-themed accommodations, each of the hotels an ode to Britain's greatest statesman
- Explore the complexities of history with a specialist Churchill guide
- Delight in the relaxed pace with free afternoons to explore London and other personal interests in England
Detailed Description
Sir Winston Churchill was the master statesman, the man who held a nation together through WWII and commanded the Allied war effort in Europe. Named the Greatest Briton of all time by the British public, Churchill was arguably the 20th-century's most influential figure. This handcrafted tour of England is more than just a journey through his life and times; it's an itinerary that celebrates the patchwork of British life and style, taking you from stately homes to quaint villages, labyrinthine tunnels to stylish art collections. You'll explore the bunkers and command posts where world history was shaped, along with discovering a private side to a very public figure. As Churchill famously said, “we make a living by what we get, but we make a life by what we give,” and so much of this legendary statesman is dotted across London and Southern England.
Running at a relaxed pace, this 8-day tour offers unique closed-door access to chapters of the Churchill legacy. You'll journey through the decades, discovering his ancestry and early years before following the trail into his role as commander of the British army in both World War I and II. This was a man with legendary motivation, a figure that enthused a nation through his radio speeches: “we shall defend our island... we shall never surrender.” And yet behind the facade is intriguing complexities. You'll see scratch marks etched into his chairs, war rooms untouched since 1945, and the historic school that shaped the man. Guided by a Churchill specialist, this intimate tour offers closed-door access and an opportunity to discover attractions rarely witnessed by the public. Spreading the vacation over eight days also provides ample time for you to explore other British attractions at your leisure, particularly those around London.
The musty smells, the historic aircraft, the moving 12th-century tunnels used in WWII; parts of the tour reflect on Churchill's role in shaping world history. Others provide an indelible insight into his private life and style, revealing everything from art collections to taste in furniture, cigar choice to ancestral palace homes. History unravels and each stop also builds a picture of iconic England. Explore iconic sights, from majestic Blenheim Palace to an art studio in a quaint Chartwell village, gargantuan hangars of planes to stylish terraces for sipping evening drinks. Even the accommodation is Churchill-inspired, ensuring you're always immersed in the style of Briton's legendary hero.
Five nights of this tour are spent in London, with relaxed excursions to a variety of attractions and significant destinations in and around the capital. You explore the lush green countryside of Kent, Churchill's birthplace, spending the night in a timeless English village. Explore England's last outpost, Dover, where the towering sights are complemented by another night of charming rural accommodation.
Click here to browse additional England itineraries we offer, and gain inspiration to craft and perfect your own dream England vacation.
Starting Price
$4,600 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
What's Included
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Verified Traveler Reviews
Based on 32 reviews
After working with Zicasso-matched travel companies in the past, I expected a worry-free and bespoke experience with this tour operator. My requests were not out of the ordinary in any way. I had wanted to explore the Cotswolds, visit Stonehenge, and then spend a couple of days in London. I had expressed that in London I was interested in seeing Abbey Road, spending a day on Military History for my son, and then a day exploring London neighborhoods and neighborhood bakers for me.
The tour operator planned transportation for us to and from the Cotswolds, a bike tour in Oxford, and a punting trip, and then two guided days in London (including a tour of the Churchill War Rooms that I had requested). In the weeks leading up to the trip, I had received a more detailed itinerary, and it was clear that days in London were not planned to specifications and were very generic offerings. And there was no effort made to accommodate my request to see Abbey Road (basically, I would be left to squeeze it in on my own). I emailed my disappointment to the tour operator, and they assured me that they would make changes to allow for my desire to explore neighborhoods and bakeries. I also wanted to get to London earlier and remove a stop in Bath and was charged a change fee (to remove something, six weeks in advance?)
Upon our arrival at Heathrow, our transportation was not onsite, which is fine; however, there was no one tracking our flight and no proactive notification that our transportation would not be able to meet us. I had to contact the tour operator's emergency line (which was very helpful).
Our second morning (Saturday), while still jet-lagged, we were up and ready to meet our driver at 9:15 in front of our hotel to take us to the train station a few towns away. Our driver was 10 minutes late, with no proactive contact to let us know that he was on his way. Then, later that day, once we were in Oxford for our bike tour, the tour company was not expecting us and did not have bikes ready for us. (Another group was there and were the only ones expected.)
The next morning (Sunday), we were told to be ready and checked out of our hotel by 9:00 a.m. for a driver to take us to see Stonehenge. At ten after 9:00, I contacted the after-hours number to inquire as to why the driver was not there. At 9:30, the tour operator still could not get in contact with the driver and recommended that I try to find a taxi to take me 2 hours away to Stonehenge. Needless to say, it was impossible to find someone at the last minute on a Sunday morning during high season. (Sidenote: a number of guests were being met by their drivers, on time, at our hotel. So, not an impossible ask.) Finally, after waiting for 3 hours, we were met by another driver who drove us to London directly. We wasted our morning (and because we had checked out of our hotel, we basically sat with our bags in the lobby) and never saw Stonehenge.
When we were in London, while our guide was a lovely person, we were asked to figure out our own way to meet her (instead of being met) and she did not have any particular knowledge about Military History (when we were in the Guards Museum, another guide was there with his party and it was clear, again, that it was not an impossible ask to have a guide with such knowledge). Also, it was clear to me that our guide, who would be guiding us for the following day, was not briefed or prepared to give a tour of neighborhood bakeries. (She thought I wanted to see a blue door in Notting Hill that was highlighted in a movie.)
All in all, I feel like I paid a premium for a vacation that I could have planned myself and instead of a stress-free and customized experience, I had to keep on top of our transportation plans and was given something perfunctory.
The tour operator has refunded me for the drive to Stonehenge that did not happen and some change fees. This seems to be an obvious gesture and the least they should have done.
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Every hotel had beautiful grounds and views. We had asked for hotels that also had the ambiance of age and antiquity. One of our favorites was in Chelsea. The staff was especially warm and friendly. We felt very comfortable with everyone! We loved all of the rooms in the entry level. It was cozy and beautiful, even the patio.
The Broadway hotel really blew us away. It was built in 1300 or so. It has an outstanding courtyard and landscaping. The staff were flexible. Theye even helped me to find a secluded area for dinner the last evening. We were mesmerized by every sitting area. There were antiques everywhere; I should say ancient antiquities. The coastal hotel was nautical and charming. There were lovely staff there as well! The views of the estuary were stunning. At high tide, the river came right up to the outdoor patio. It was mesmerizing!
Another hotel was very pretty inside and had compelling views of gardens and sweeping lawns. It overlooked the Jurassic coast, as well as a very large beach and piers. It was very far to walk and straight downhill. We could not get any taxi or bus to get to the harbor for our boat ride, sadly. We tried walking, but it was too far. There was no taxi for the return trip either. We had to walk up steep steps and then along a winding garden path back to the top. It was very stressful for me because I have a damaged tendon in my ankle, which hurt me quite a lot. It was very disappointing. However, my husband was thrilled that I made it up the hill. So was I.
There was a mix-up at the hotel about our room. We had discussed with our agent that we needed rooms on the ground floors. They had us on the first floor and moved us at the last minute to a very small corner room with cheap furniture and no space for two people to maneuver. We were both appalled, but fortunately our agent was able to take our call and we ended up in an apartment instead. It had no view other than of parked cars, but it was spacious and modern. It was the best they could do. This hotel was located in Lyme Regis.
Our next stop was Henley on Thames. The hotel was very nice and the two was pretty, but we didn’t arrive until 4.30. There was no Sunday dinner, so went elsewhere. Then we left the next morning at 9.30. The river was lovely to view.
We had fantastic drivers and driver guides throughout London, the Cotswolds, Cornwall, and Dorset back to London.
We missed our tour of Westminster Abbey due to the time change and lack of sleep. Our concierge tried his best to arrange for us to visit it on our last day. I called our travel company and was given the ticket number by email. Westminster Abbey declined because the company it was purchased through refused to confirm it. We were again disappointed. I tried calling the travel company back, left a message for help, but never got a return call.
We may go back again, but I would arrange for someone to meet me at the airport with a wheelchair. I would have been less stressed. That airport was overwhelming and confusing.
I sincerely wished that we did not have the Chelsea Flower Show and Windsor Castle on the same day. I could hardly walk by the end. Our agents offered to change Windsor to a different day, but it was an additional £350 or so. That seemed very unfair.
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Zicasso's travel company helped create a wonderful UK trip for my family. Their fine attention to detail, along with a spectacularly planned itinerary, was greatly appreciated. From our drivers to amazing tour guides - the one in White Cliffs of Dover, the one in Ireland, and the one in Scotland - this trip was spot-on perfect!
The travel company's app was extremely helpful and user-friendly, and the lodging facilities chosen were perfect. In particular, the hotels located in the heart of each city made walking tours and exploring ideal. In addition, pre-planned excursions and activities added to an overall positive experience.
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We had an excellent visit. Having been in London previously, we limited our activities to museums, plays, tours, and dining. Zicasso's travel agency was very responsive to our requests. We were most appreciative of the six-night hotel selection, which was ideal for getting around. Being next to the centrally located Charing Cross Station and the provided Oyster cards made navigation a pleasure.
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Zicasso's trip planner worked with my family for the better part of a year planning our big family trip. She provided exceptional service and planned every detail of our trip. We have a large family, with lots of moving parts. There were many changes in the itinerary along the way and she rolled with all the many changes. She was always polite, courteous, and graceful in her many interactions with our family.
She listened carefully during our initial conversations to help us plan the best trip possible. Being a large family, with multiple generations, she really created the best possible experience, taking in everyone's wishes. Working with her was very relieving, knowing she was taking care of all the details.
Our family's trip took us from the States to Ireland, Scotland, and England. We traveled on planes, trains, ferry, and drove a car. Our trip planner arranged every detail meticulously. We stayed in lovely, quaint, boutique hotels, ate the most wonderful foods, saw the amazing sights, and UNESCO World Heritage Sites across all three countries. From the Cliffs of Moher to the Culloden Moor Memorial to Stonehenge to castles grand and desolate; from beautiful cathedrals to old abbey ruins; from little country pubs to Michelin-starred restaurants; and even spending a couple days in an actual 17th-century castle, every minute was amazing! Truly amazing!
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We absolutely loved our England adventure and already wish we could go back. It was a perfect balance of English countryside, history, and culture.
All our hotels were wonderful. The lodge in Broadway was such an extraordinary place to stay—the property was so historic, but the rooms and amenities were modern. We loved the pool and gym, and delicious food/drink they offered. We also took advantage of the playground down the street every evening after dinner—it had a zipline and a beautiful vista. The lodge at Warwick was also amazing, such a fun place to stay for families with young kids. We also really enjoyed our hotel in London. The location was ideal as we could walk to restaurants and we had a tube station right there.
Our drivers were also very professional and friendly, and made the transfers between locations so simple and stress-free for us. Honestly we have nothing but good things to say about every moment of this vacation, from the afternoon tea to the "Harry Potter" studio tour.
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