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 17 reviews
Our trip to England was fantastic! We traveled with my parents and my two teenaged boys. We only had 10 days for the trip, so we decided to keep our destinations relatively close together. Our travel planner did a great job of listening to our must do items and weaving together an itinerary that hit everything without exhausting us. They were very prompt in responding to any questions or changes and we were never left hanging.
We visited London, Stonehenge, The Cotswolds, Stratford, and Oxford. During our four days in London, we went to Westminster Abbey, the Churchill War Rooms, Tower of London, St. Paul's Cathedral, Buckingham Palace, Kensington Gardens, and The British Museum. We saw two shows in London, one at the Globe and another right by Piccadilly Circus. From there, we went to Hampton Court, Stonehenge, spent the night at a Castle in South Gloucestershire, took a tour of The Cotswolds, took in all things Shakespeare in Stratford, visited Blenheim Palace, Windsor Castle and had an owl evening at a falconry center where we got to handle and 'fly' several owls. The trip was a perfect mix of city and country without having to drive hours on end.
The travel planner sent us a binder a couple weeks out from the trip with each day mapped out with our itinerary for the day, then any tickets or directions we would need for that day. It was extremely organized and made everything very easy to keep track of. They had suggestions for activities and places to eat, which were very helpful.
The trip was wonderful and everyone in the family loved it!
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Overall, this travel company provided a fantastic traveling experience. We were able to enjoy many of the iconic attractions in London, including the London Eye, Westminster Abbey, Churchill War Rooms, and the Tower of London, as well as explore on our own. We also enjoyed afternoon tea and wonderful play in the West End! In addition, they provided some wonderful dining recommendations that turned out to be a few of our favorite meals!
Beyond London, we were able to explore numerous towns and villages in the southern England, including Thornbury, Cheddar, Bath, the Cotswolds, Winchester, and Windsor.
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This travel agency planned an excellent London, Bath, and multiple side-trip vacation for me and my family. The logistics were well-designed and executed. The tour guides were well above average, and the hotel choices in London and Bath were perfect.
We spent five nights in London, three nights in Bath, and our final night in Oxford.
Our side-trips from London included a day visiting sites related to the life of Jane Austen (Steventon, Chawton, Winchester, and Lacock) and day traveling south to visit Leeds castle in Kent, the Canterbury Cathedral, and the Dover Cliffs.
Our final day side trip took us from Bath, through Bradford-on-Avon, to Stonehenge, Highclere Castle, and then ending the day in Oxford.
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We have used this travel company several times and Lindsey and her team continue to impress. The itineraries are creative, the service is impeccable and quick, and they truly listen.Part of our most recent trip we were traveling to England with our two grandsons (ages 7 and 5). Lindsey arranged for a kid-oriented pre-opening tour of the Tower of London. After we entered we were the only tourists in the Tower until it opened to the public 45 minutes after we arrived. They literally closed the gates after we entered and were greeted by our private Yeoman Warder. We walked with him, asked questions and immediately went to the storehouse for the Crown Jewels and had a private tour of the complete display. We couldn’t believe we were the only ones there! The guide was excellent and had a booklet with things the kids were supposed to find as we toured. They were very engaged and they are still talking about it.Earlier on our trip we were in the Loire Valley of France celebrating milestone birthdays with 30 friends and family at a chateau. The trip had been postponed to 2022 from 2020 due to Covid. After the hell of the last two years we asked Lindsey for ideas to make the Loire portion of our trip extra special. She suggested a wine tasting cruise on the Loire River with a sommelier, Loire Valley wines, food pairings, and musical accompaniment. Wow was that fun and our friends had the time of their lives as did we.A few days before we were to leave France via plane to England, the French airport workers called a strike for the day we were to fly. We contacted Lindsey who immediately arranged for us to change from taking a plane to taking the Eurostar train instead. And the plane fare was refunded before we got home.We travel a lot. When we travel we look for unique experiences and hassle-free travel. This travel agency has met our expectations and exceeded them every time we use them.
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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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