Westerham might be a charming town in Kent, but its real appeal lies in its proximity to some truly fascinating day tours. Whether you’re a history enthusiast, a fan of royalty, or simply looking to enjoy the quintessential English countryside, Westerham offers excellent options. The tours listed here stand out because they combine rich history with personal experiences, often in small groups or private settings—making your day feel both special and authentic. I especially like the private nature of these trips, like the London: Hever Castle & Chartwell House Private Day Tour, which offers a tailored experience exploring Anne Boleyn’s childhood home and Winston Churchill’s retreat.
In this guide, we’ll cover two of the best tours available from Westerham: one that blends the grandeur of castles and stately homes with scenic countryside drives, and another that offers a deep dive into Churchill’s life at his beloved home. Both cater to history lovers and those seeking an intimate experience, but each has its own unique flavor.
1. London: Hever Castle & Chartwell House Private Day Tour
This private day tour from London is a fantastic way to learn about English history without the hassle of organizing multiple visits. For around $494 per person, you’ll enjoy a 10-hour trip that covers two iconic sites: Hever Castle, the childhood home of Anne Boleyn, and Chartwell House, Winston Churchill’s country retreat. The tour includes hotel pickup and drop-off, making it one of the most convenient options.
What sets this tour apart is the personalized approach—your private guide will take you through the castle’s stunning gardens, lakeside paths, and interiors rich with Tudor history. It’s a great choice if you love castles and want a flexible schedule. Afterward, you’ll head through the lush Kent and Surrey countryside, with plenty of photo stops along the way. At Chartwell, you’ll explore Churchill’s home, including his gardens and the rooms where he painted and worked. The scenic drive between sites offers a peaceful glimpse of rural England that many visitors miss.
The value is clear: a private, tailored experience for those who appreciate comfort and detailed stories. This tour is ideal for travelers who want to combine history, scenery, and a hassle-free day in one package. Expect to spend a full day on this adventure, making it a bit more expensive but well worth the price for the intimacy and flexibility.
Bottom Line: If you want a comprehensive, private experience visiting two of England’s most storied sites in one day, this tour hits the mark.
2. Private Day Tour to Chartwell, Home of Sir Winston Churchill
For around $1,131.47 per group (up to four), this private tour offers a deep dive into the life of one of Britain’s most famous figures: Winston Churchill. Starting from Westminster, the tour includes about seven hours exploring Churchill’s beloved home and studio. The highlight is the chance to see Chartwell House as it was during Churchill’s most active years—with many rooms preserved to reflect his personal life.
What makes this tour unique is the focus on Churchill’s artistic side. You’ll visit his famous studio, where he painted over 500 works, and view a large collection of his paintings. The guide, who is passionate and knowledgeable, will walk you through Churchill’s stories, sharing insights about his leadership, personal struggles, and creative pursuits. This tour also includes walking in the footsteps of Churchill, Charlie Chaplin, and other notable figures who visited the estate.
This experience suits travelers who want a more intimate, in-depth look at Churchill’s life, especially if you’re interested in art and personal stories. The route includes a lunch break at Chartwell, giving you time to absorb the surroundings. One review termed it “a fascinating glimpse into Churchill’s world,” confirming the tour’s appeal for history and art buffs alike.
Bottom Line: For Churchill fans or those seeking a personal connection to Britain’s wartime leader, this comprehensive private visit is hard to beat.
How to Choose Between These Tours
If your goal is to visit two historic sites in a single day with minimal fuss, the London: Hever Castle & Chartwell House Private Day Tour offers great value, especially with its private, flexible approach. It’s perfect for those who want a broad overview of Tudor and WWII history combined with scenic countryside views.
On the other hand, if you’re fascinated by Winston Churchill and want to focus solely on his life, the Private Day Tour to Chartwell delivers an immersive experience. It’s pricier but ideal for travelers eager to explore Churchill’s personal and artistic world.
When choosing, consider your budget, time available, and specific interests. For example, history buffs interested in Tudor England might prefer the first tour, while Churchill admirers or art lovers could find the second more rewarding. Booking early is advisable for these private and popular tours.
Westerham offers a great starting point for exploring England’s rich past. Whether you choose a private castle and Churchill tour or a dedicated Churchill experience, you’ll leave with a deeper appreciation for this country’s storied history. Both options give a personal touch and plenty of opportunities to ask questions—so don’t wait, book early, and enjoy your day among England’s most iconic landmarks.
