Chartwell & Hever Castle Day Tour
Discover the homes of Sir Winston Churchill and Anne Boleyn on a private day tour through the beautiful Kent countryside.
Step into the world of Sir Winston Churchill and Anne Boleyn on a private day tour through the beautiful Kent countryside. Travel with your dedicated driver and expert guide as you discover Chartwell, Churchill’s cherished family home, and the magnificent moated Hever Castle, one of England’s finest historic estates.
£1,095 per private group
1–6 guests · Larger groups by arrangement
Approx. 9 hours · Mercedes V-Class · Dedicated driver & expert guide
Entrance tickets additional
Expert Driver & Guide
Local knowledge that brings every destination to life.
Private Travel Experience
Comfortable touring at your own pace with no groups.
Tailored Itineraries
Every journey personalised to your interests and travel style.
Personal Planning Support
Planning support before and during your tour.
Tour Overview
Enjoy a private day exploring two of Kent’s most iconic historic estates. Visit Chartwell, the cherished former home of Sir Winston Churchill, where his life, legacy and gardens come vividly to life. Continue to Hever Castle, the picturesque childhood home of Anne Boleyn, set within a stunning moated estate and beautiful formal gardens.
Travel in chauffeur-driven comfort through the Kent countryside as your expert guide shares stories of royal intrigue, political history and English heritage, creating a relaxed, informative and memorable day beyond London.
Tour Details
Duration
Full Day (10 hours)
Starts & Ends
Your London hotel or preferred central London location
Group Size
Private tour for individuals, couples, families and small groups
Travel Style
Private vehicle with your dedicated driver and expert guide
Places You'll Visit
Discover two of Kent’s most remarkable historic estates, where Churchill’s twentieth-century legacy meets the Tudor world of Anne Boleyn. Explore elegant gardens, remarkable collections and centuries of English history in one unforgettable day.
Churchill’s Countryside Retreat
Chartwell offers a rare glimpse into the private world of Sir Winston Churchill — statesman, writer, artist, and family man. Every room tells a story, while the surrounding gardens and lakes reflect Churchill’s lifelong love of the English countryside.
Churchill’s Home
Explore the house preserved much as it was during Churchill’s lifetime. See his books, photographs, and personal mementoes that reveal the man behind the leader.
Paintings and Collections
View the largest collection of Churchill’s paintings, alongside treasures gathered from his travels, military career, and political life.
Hillside Gardens and Lakes
Wander the peaceful gardens Churchill designed himself — from the lakes he created to the kitchen garden and Marycot playhouse built for his daughter Mary.
Churchill’s Home
Explore the house preserved much as it was during Churchill’s lifetime. See his books, photographs, and personal mementoes that reveal the man behind the leader.
Paintings and Collections
View the world’s largest collection of Churchill’s paintings, alongside treasures gathered throughout his military career, political life and extensive travels.
Hillside Gardens and Lakes
Wander through the peaceful hillside gardens Churchill designed himself, discovering ornamental lakes, the kitchen garden and the charming Marycot playhouse built for his daughter Mary.
The Tudor Legacy of Hever Castle
A short, scenic drive from Chartwell takes you to Hever Castle — a storybook moated estate with deep royal roots. Once home to Anne Boleyn, it stands as a testament to love, power and ambition that changed the course of English history.
Tudor Heritage
Step back to the 13th century and explore the castle’s panelled rooms filled with fine furniture, tapestries, and an outstanding collection of Tudor portraits.
The Book of Hours Room
See Anne Boleyn’s personal prayer books, beautifully illuminated and inscribed in her own hand — a poignant connection to her life and faith.
The Astor Legacy
Discover the story of William Waldorf Astor, who restored Hever in the early 1900s. The Astor Suite displays art, photographs and memorabilia from this elegant Edwardian chapter.
Tudor Heritage
Step back to the 13th century and explore the castle’s panelled rooms filled with fine furniture, tapestries, and an outstanding collection of Tudor portraits.
The Book of Hours Room
See Anne Boleyn’s personal prayer books, beautifully illuminated and inscribed in her own hand — a poignant connection to her life and faith.
The Astor Legacy
Discover the story of William Waldorf Astor, who restored Hever in the early 1900s. The Astor Suite displays art, photographs and memorabilia revealing how one of England’s great country houses was lovingly restored for the twentieth century.
Suggested Day Itinerary
A relaxed, expertly guided day designed around your interests, with comfortable private travel throughout.
Chartwell & Hever Castle
Morning – Chartwell
Depart your London hotel, airport or Southampton Cruise Terminal and travel through the beautiful Kent countryside to Chartwell, the cherished home of Sir Winston Churchill. Explore the house, Churchill’s studio, personal collections and the gardens he designed, learning about the remarkable life of Britain’s wartime leader.
Midday – Lunch & Gardens
Take time to enjoy Chartwell’s hillside gardens, lakes and peaceful estate before continuing to Hever Castle. Lunch can be enjoyed at Hever Castle or at a carefully selected country pub, depending on your preferences and the day’s schedule.
Afternoon – Hever Castle
Discover Hever Castle, the childhood home of Anne Boleyn. Explore the Tudor rooms, the Book of Hours Room and the Astor Collection before wandering through the Italian Garden, Rose Garden, lakeside walks and magnificent moated grounds.
Return Journey
Relax as your dedicated driver returns you comfortably to London after an enjoyable day exploring two of Kent’s most fascinating historic estates.
“What a FABULOUS day it was! Our guide, Roy, did an excellent job of guiding us around the Cotswolds. He was very knowledgeable, pleasant and accommodating. We thoroughly enjoyed our experience.”
Kathleen Maledon – Phoenix, United States
Frequently Asked Questions
Yes. As this is a private tour we can adjust the pace of the day, allow additional time at either Chartwell or Hever Castle, and tailor the itinerary to suit your interests.
Most tours start from central London, with pickup from your hotel or private residence. Alternative starting points can be arranged upon request.
The experience typically lasts around 10 hours, including travel between London, Chartwell and Hever Castle.
Lunch is not included, but we are happy to recommend and reserve a traditional country pub or restaurant near Hever Castle, subject to availability.
You will travel in a comfortable private vehicle with your dedicated driver and expert guide. Vehicle choice depends on your group size and luggage requirements.
Click the “Enquire About This Tour” or “Plan Your Private Day Tour ” buttons on the page. We provide a detailed, customised itinerary and pricing once we understand your preferences.
Start Planning Your Private Day Tour
Tell us your preferred travel date, group size and any special interests. We’ll prepare a personalised itinerary and quotation with no obligation.