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Behind the Glass of Churchill’s Life


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  • Visit the War Cabinet Rooms with the Director before they are opened to the public
  • Day trip to Windsor for a tour of the castle, followed by High Tea with an Old Etonian who can shed light on what it was like to be educated there
  • Stay in Winston Churchill’s favourite London Hotel – the majestic Brown’s
  • Enjoy a privately guided tour around St James’s, visiting the speciality shops Churchill so loved
  • Spend an evening wine tasting at Berry Brothers – his favourite wine shop
  • Enjoy a day trip to Blenheim Palace, the place of Winston Churchill’s birth

What’s Included

  • 5 nights Bed & Breakfast
  • 4 days of private guiding
  • Tickets to all the sites
  • Wine Tasting Experience
  • High Tea at Eton
  • Private Guide for Windsor Castle and Blenheim Palace
  • All private transfers
  • International Economy class flights

Example Itinerary

London, England

  • See the city of London through Churchill’s eyes
  • Enjoy nights at his favourite hotel and their special in house cocktail, a Churchill martini

It will come as no surprise, being the capital city, that London holds the most significant Royal and Parliamentary seat of power.

For the duration of your time in London, you will stay at Churchill’s favourite hotel, Brown’s. He was also partial to stopping by for a tipple after a stressful day in office. So today, Brown’s Donovan Bar cocktail menu contains a number of special dedications to valued guests, including the Churchill Martini. The hotel was also a particular favourite of the Roosevelt family. Both Theodore Roosevelt, the 27th President of the United States, and Franklin Roosevelt, the 32nd President of the United States, visited before they were elected.

A Day at the War Rooms

During your first full day, you will rise early for a tour of the Churchill War Rooms before they are opened to the public for a private tour with the museum’s director. During the Second World War, a group of basement offices in Whitehall served as the centre of Britain’s war effort. The complex, known as the Cabinet War Rooms, was occupied by leading government ministers, military strategists and Prime Minister Winston Churchill. Today, the museum has been created in situ with one room exactly as it was on the day they ceased to operate, Victory Day. The highlight of your tour will be the opportunity to go behind the glass of the room where the decisions were made, and sit for yourself in the exact chair that Winston Churchill oversaw meetings from.

In the afternoon, you will travel to St James Place for a tour of the area and the specialist shops that Winston Churchill so loved. Paxton and Whitfield Cheese Shop on Jermyn Street, Lock & Co Hatters (who made the hat he wore on his wedding day) and Berry Brothers & Rudd, his preferred place to purchase wine. Following this, it will be time to put your feet up and enjoy a well earnt British High Tea at the Ritz – Churchill’s favoured in the whole city.

Windsor Castle and English Tea

You will leave London for Windsor with an expert guide to accompany you. Windsor Castle is still very much a working castle, and is the favourite home of Her Majesty the Queen. The magnificent state rooms provide an overview of architectural and interior design over the centuries and there is no shortage of stories about the characters who once filled these rooms. Windsor town is also a perfect place for some souvenir shopping. Following your tour, you will stop for more English Tea and cakes with an Old Etonian who will be able to shed light on what it is like to be educated at one of the world’s most famous schools. Of course, this is where Sir Winston Churchill was educated.

Blenheim Palace

The next day brings another day trip out of the city, this time to Winston Churchill’s birthplace – Blenheim Palace. A masterpiece of eighteenth century Baroque architecture, Blenheim Palace is home to the 12th Duke and Duchess of Marlborough and the birthplace of Winston Churchill. The work of the famous “Capability” Brown, there is something for all the family with pleasure gardens, formal gardens, parkland and the Marlborough maze to enjoy.

Take your final day in London at your own pace, before returning home.


It was my third visit to London and the first that True Travel had organised. Planning was seamless and our guide gave an added insight that you would never get from a guidebook. The whole team loved the trip – thank you to Molly for planning it and it was great to be able to meet you too!

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