Located a mere five miles from each other, Sir Winston Churchill’s former home at Chartwell and Hever Castle, (once owned by the Boleyn family), represent two of the most important historical sites in all of England. On our tailor-made Kent day tour, you will take a deep dive into English history — all in the company of an expert local guide.

At Chartwell, you will gain an intimate understanding of Churchill’s life and motivations; you will also get to experience the great Prime Minister’s creative side as Chartwell is home to the largest collection of his paintings found anywhere in the world.

At Hever Castle, we will explore England’s medieval past and the Tudor-era, and we’ll encounter a range of colourful characters from across the centuries.


Chartwell: The Treasured Country Home of Sir Winston Churchill

The National Trust, Britain’s primary organisation for the preservation of heritage, regard Chartwell as one of the greatest houses under their care. This is fitting, as Chartwell is the former home of one of Britain’s towering political and historical figures, Sir Winston Churchill. It is no exaggeration to say that Churchill ranks alongside the likes of William Shakespeare, Queen Victoria, and Henry VIII as one of the most iconic characters in English history. 

Famous across the world primarily for his leadership during WWII, Churchill was an endlessly complex person. An aristocrat, historian, linguist, painter, politician, First Lord of the Admiralty, and drinker of legendary quantities of champagne and scotch, the high adventure of Sir Winston’s life is almost too grand to be believed. Yet, the facts here are truly more extraordinary than fiction. And had it not been for this larger-than-life leader, the fate of the free world would have, undoubtedly, been very different.

Sir Winston Churchill’s statue in nearby Westerham, Kent.

The beauty of a visit to Chartwell lies in the insight it gives to Churchill at his most creative. Here guests encounter Churchill as a family man, writer, and, of course, as a gifted pastoral painter.

Since the National Trust took responsibility for maintaining the property in the late 1940s, they have lovingly worked to preserve the things that make this property such a treat for anyone interested in the life of Sir Winston Churchill, or British history in general.

Inside the home, you can get a feel for how the Churchill family lived, you can see the very desk where Sir Winston composed many of his iconic speeches, and explore collections of art and antiques. While outside you can enjoy the peaceful natural surroundings that inspired Churchill as an artist.

Travellers particularly interested in the life of Churchill may wish to consider our Private Tour to Churchill’s Chartwell, a shorter tour focused entirely on Chartwell. 

Hever Castle

Hever Castle: Turbulent Tudors and Pristine Gardens

There’s no shortage of beautiful sites in Kent, the garden of England. Hever Castle, though, unquestionably ranks among the county’s great jewels, an atmospheric and historic destination that has long been a favourite of our guests here at John England Tours. Join us for a private, guided tour of the castle and we’ll walk through the great halls and rooms of the castle’s interior. With the home dating back to the 13th century, it’s no surprise to learn that this has been the location of many dramatic chapters in England’s history, particularly in relation to the monarchy. 

Hever Castle was once the childhood home of Anne Boleyn, the second wife of King Henry VIII and mother of Queen Elizabeth I. Henry VIII would often reside at the nearby Bolebroke Castle as he began to court Anne (a courting that would lead to marriage, queenship, and, infamously, Anne’s beheading). 

Dining Hall at Hever Castle

The castle’s history will be brought to life as you gaze upon centuries-old tapestries, furniture, and room upon room of antiques (including two prayer books belonging to Anne Boleyn, signed with her name). It is also here that you will be able to get up close to many of the Tudor age’s most famous personalities as Hever Castle is home to one of the greatest collections of Tudor portraits. And some even say that among these historic objects, a ghost can occasionally be encountered — is it Anne Boleyn herself? 

You will also learn about the castle’s recent history and its time in the possession of the wealthy American businessman William Waldorf Astor, whose passion for the property and deep pockets ensured its restoration. After an exploration of the interiors, we can then enjoy the site’s immaculately kept gardens, some of the finest in all of England. 

Join us for a visit to Hever Castle and leave with a rich new insight into several extraordinary periods in English history, such as the Wars of the Roses, Henry VIII’s reign, and the Reformation. This picture book castle is sure to fire the imaginations of all visitors, young or old.

This tailor-made guided tour is an ideal choice for any visitors to England interested in the nation’s history. While our range of Private Tours shines a light on many chapters in British history, this day tour of Chartwell and Hever Castle is notable for how much variety you will enjoy on a single trip. From the height of the middle ages through to the death of Churchill in the 1960s, this tour navigates the breadth of England’s tumultuous past.

If you have any questions or comments regarding this tailor-made tour, please don’t hesitate to contact us.

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