Sir Winston Churchill Tour of England

A 8 day trip to England 
5 out of 5 stars
1 reviews

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. 

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General Information

Detailed Itinerary

Places Visited 

London, Churchill Bar & Terrace, Harrow School, Blenheim Palace, Bladen, Kent, Westerham, Chartwell, Dover, Dover Castle, WWII Tunnels, Cabinet War Rooms, Whitehall, Imperial War Museum, Bletchley Park, Uxbridge Barracks, RAF Hendon

Departure Dates 

Dates are flexible and customizable for private departure. 

Detailed Itinerary 

Day 1: 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. Consider learning more about the best England travel agents whom we partner with, and see how they are able to tailor your dream England vacation to your particular interests and desires. 

What's Included: airport transfer, accommodation

Day 2: London – Historic Harrow School and Seven Prime Ministers

Harrow School is an ode to old-world England, the corridors lined with thick oak panels and every building exuding an air of grandeur. Seven prime ministers were educated here, including Churchill in 1888. At the fourth-form classroom, you can read the famous names, each of them carved into the panels along the wall. With its majestic furnishings, it almost feels surreal that this is a working school; it doesn't come as a surprise when your guide points out that this classroom was a filming location for Harry Potter and the Sorcerer's Stone. You enjoy a private tour of the school before returning to London for a relaxed afternoon in the capital. Exploring all of London could take a lifetime and every visitor has their own idea of famous or unseen sights to see. Throughout the itinerary, you have the free time to piece together your own version of London, with your guide also offering a helping hand.

What's Included: accommodation, transfer, tour, breakfast

Day 3: London – Day Trip to Oxfordshire – Private Tour of Blenheim Palace and Churchill's Resting Place

Blenheim stands resplendent and unbowed, delighting in its early-18th-century glory. Turrets stand on top of Romanesque pillars, faded stone hangs above manicured lawns, and every wall feels like a blueprint for the English Baroque style. This is England's finest stately home and deserves its UNESCO World Heritage status. Explore the regal interiors, admire oil portraits framed in gold leaf, and revel in the architectural excess of the age. But you're not just here to discover royal England. This is the home of the Spencer-Churchills and the birthplace of Winston Churchill. Ancestral figures dot the walls, large portraits of 17th-century dukes and alluring duchesses. As your guide narrates the figures, there's a keen sense of the Churchills' reputation as military commanders. You'll enjoy exclusive closed-door access to private parts of the palace that intimately reveal the stories behind the name.

Throughout the palace, there are special exhibitions dedicated to Winston Churchill and his ancestors, helping you unravel a family tree that has been long honored for defending the British nation. Returning to the pomp and glamor of the palace, you enjoy traditional afternoon tea in the Indian Room, an indelible tradition that brings a tiered silver platter of artisanal treats to your table. Before returning to London, you stop in nearby Bladen. Winston Churchill is buried in the village churchyard, and his grave is somewhat understated given the size of his funeral. At the time, his state funeral attracted the largest assembly of world statesmen in history. Perhaps Churchill doesn't require an elaborate grave; after all, this is the man who declared that “history will be kind to me, for I intend to write it.”

What's Included: accommodation, transfer, tour, breakfast

Day 4: Kent – Exploring Churchill's Family Home

Today you move forward through the decades, journeying into the lush green countryside of Kent and the cute village of Westerham. Winston Churchill's home remains untouched since his death, carefully preserved to offer a revealing insight into his personal life. An art studio is strewn with paints and brushes, photographs stand proudly beside a revered cigar collection, and thickly-packed bookshelves dominate many walls. There's an air of regality to some of the interiors, but the house mostly reflects on how Churchill was a deeply private man behind closed doors. Continue into the Kent countryside, stopping at the Churchill statue on the village green of Westerham, and then spend the night at an ornate 17th-century mansion surrounded by postcard images of rural England. The afternoon is free, and there are countless trails to take through the private grounds.

What's Included: accommodation, transfer, tour, breakfast

Day 5: Dover – Incredible WWII Tunnels and Evocative War History

Dover Castle stands imperious, gazing across the Channel with the same indomitability it has had since the 12th-century. Moving along white cliffs, you enter the castle and then duck through a small darkened trapdoor. Beneath the stone is an eery maze of tunnels, damp, musty, and resonating with importance. These tunnels were built at the same time as the castle, a medieval time that produced corridors used in countless battles over the centuries. Remarkably, it was from these tunnels that Churchill planned and commanded Operation Dynamo, rescuing some 338,000 men from the beaches of France in 1941. Extensions and improvements were apparently made over the centuries, but you can sense how the tunnels have been utilized across British history. 

Churchill is famed for his role as British prime minister during World War II. But he also commanded the Admiralty during the first world war, motivating and organizing with his indelible sense of calm. “If you're going through hell, keep going” was just one of his phrases that soared through the trenches as Churchill's role morphed into wider control of British troops. From Dover Castle, you'll enjoy an elegant lunch with views onto the water, before being transferred to the five-star Bed & Breakfast. You're now on the outskirts of historic Canterbury, home to a World Heritage cathedral dating from the 11th century. The afternoon offers a chance to explore this preserved village at leisure; the evening choir song fills the old stone with a redolent charm.

What's Included: accommodation, transfer, tour, breakfast, lunch

Day 6: London – Churchill's Remarkable Cabinet War Rooms

As you admire Churchill's chair, there's a strong sense of the pressure he was under. Scratch marks are torn into the leather, matching those carved into the desk. An immortal quote offers an explanation: “the price of greatness is responsibility.” Churchill's Cabinet War Rooms are found beneath Whitehall, and they've been left untouched since 1945. Even the commander's half-smoked cigar still sits in an ashtray. So much world history was dictated from these rooms, including many of Churchill's famous radio speeches to the nation. A second specialist guide joins you for the private tour, ensuring you really unravel what took place within the austere rooms. Maps are hung across walls, bizarrely-colored telephones line desks, and strategic charts remain dotted with the odd mug stain. After a leisurely breakfast, you'll travel back to London for your tour of the war rooms. The rest of the day is at your leisure, and you return to your hotel for your overnight accommodation.

What's Included: accommodation, transfer, tour, breakfast

Day 7: London – WWII Operations Bunker and Legendary Aircraft

Today you explore the inspiring memoirs to World War II, first being guided to Bletchley Park, where a remarkable code-cracking machine stands in all its primitive glory. Ancient dials and lights reveal the future of computing – back in the 1940s – and your guide explains how this Enigma machine was used to intercept German military intelligence. Nearby is Uxbridge Barracks, a military hub regularly visited by Churchill throughout the early stages of the war. As an aerial war raged between Britain and Germany, Churchill's expert command was relayed from this austere room. You can feel the history that radiates from the walls, so many lives saved from such a small but poignant place.

Eventually, it would be the British Spitfire that ruled the air. Nearby RAF Hendon has a huge hangar filled with these aircraft, some of them carefully preserved and others left in an inspiring state of ruin. Other historical aircraft hangs from the roof, like Vickers Wellingtons and early gliders. Following the Churchill trail, you admire other engineering marvels, like the Avro Lancasters and the Lancaster Bombers. This is Britain's National Air Museum, and you could spend days exploring all the shapes and styles. After you return to London, you enjoy a Churchill-themed dinner at one of London's premier restaurants: a clear soup followed by roast game meat, topped off with ice cream with chocolate sauce. Pear and stilton cheese provides the delectable final course, and it wouldn't be a Churchill dinner without a nightcap of brandy.

What's Included: accommodation, transfer, tour, breakfast, dinner

Day 8: London – Departure

Departing England, it's hard to know which Churchill quote has most resonance. Perhaps “attitude is a little thing that makes a big difference” or maybe “to improve is to change; to be perfect is to change often.” After the immersion in the life of the greatest ever Briton, you're transferred to the airport for your international flight. Say farewell to the guide and leave England with a hundred other quotes rolling around your mind.

What's Included: airport transfer, breakfast



Zicasso recommends the following guidelines for customized England tour packages, excluding international flights:

  • 5-star: USD $400 - $1,000+ per person per day
  • 4-star: Minimum USD $350 per person per day
  • 3-star: Minimum USD $300 per person per day

The customized package will include hotels, airport transfers and other transportation within England, guided tours or activities, unique experiences, trip planning, and 24x7 support during your trip.

Please inquire for a custom quote. The price is customized based on final hotel choices, travel dates, and other custom preferences.