Parliament Square with statue of Winston Churchill in London, England

Sir Winston Churchill Tour of England

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited


Places Visited

London, Churchill Bar & Terrace, Harrow School, Blenheim Palace...

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Suggested Duration

8 Days

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...

Customizable Itinerary

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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

$3,635 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.

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