A Private Windsor Walking Tour: An Intimate Look at Royal and Town Life
Windsor, England, is one of those places where history feels alive on every street corner. This private walking tour offers a chance to explore Windsor at a relaxed pace with a local guide, uncovering the town’s royal roots and lively streets. For just over an hour and a half, you’ll stroll past iconic sights like Windsor Castle, Eton College, and the long sweeping views of the River Thames, all while getting insights from someone who knows the town inside-out.
What I find particularly appealing about this tour is the personalized approach. With only your group of up to six people, the guide can tailor the experience, answer all your questions, and share little-known facts that you wouldn’t find in a guidebook. The tour’s length makes it accessible even for busy schedules, and the cost, at about $171 for a group, packs a lot of value considering the depth of local knowledge and the chance to enjoy Windsor’s sights without rushing.
One thing to keep in mind: the tour doesn’t include entry to Windsor Castle itself. If you’re eager to step inside the castle, you’ll need to buy tickets separately, but the outside view and the detailed explanation from your guide still make it worthwhile. Also, because it’s a walking tour, be prepared for a fair amount of strolling on sometimes uneven surfaces, and wear comfortable shoes.
Key points / Takeaways:
– Personalized experience: Only your group participates, making it ideal for a tailored visit.
– In-depth local insights: A knowledgeable guide, like Eva, enriches the experience with stories and facts.
– Historic and scenic sights: From Windsor Castle and St. George’s Chapel to the quirky Crooked House and views of the River Thames.
– Flexible pacing: You can linger at favorite spots or move quickly through less interesting areas.
– Cost versus value: For around $171, you gain a private guide and intimate access to Windsor’s highlights.
– No castle entry included: Remember, you’ll see the outside of Windsor Castle but need separate tickets to go inside.
Discovering Windsor on Foot: A Guide to the Highlights

Starting Point: Windsor Guildhall
Your journey begins outside Windsor Guildhall, a central spot that’s rich with history and a good orientation point. Your guide will give you a quick overview of Windsor’s royal significance—how it’s been linked to monarchs since William the Conqueror’s time—and set the scene for the walk ahead. The Guildhall’s architecture lends a regal air, and it’s a natural starting point to feel the town’s historic pulse.
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The Crooked House of Windsor
No visit to Windsor is complete without a glance at this quirky building—often called Windsor’s version of Pisa’s Leaning Tower. It’s a quick stop, but I love how it adds a dash of whimsy to the tour. It also shows how Windsor’s buildings aren’t just about grandeur but have character and stories that make the town uniquely charming.
Irish Guardsman Statue and Local Pride
Next, you’ll see a statue honoring the Irish Guards, a regiment with deep ties to Windsor. It’s a poignant reminder of Windsor’s military connections and the town’s role in national ceremonies. It’s free to see, and your guide will fill you in on its significance.
Historic Streets and the Black Horse Inn
Walking along the Two Brewers street, you’ll pass one of Windsor’s oldest streets. This area is lined with historic pubs and buildings, including the legendary Black Horse Inn, once known for its outrageous character. Walking here, you get a sense of Windsor’s long-standing social life, blending royal prestige with everyday local traditions.
The Long Walk and Copper Horse Statue
As you stroll along the Long Walk, your guide might point out that this expansive vista was once William the Conqueror’s hunting ground. It’s a perfect spot to reflect on Windsor’s royal past while enjoying stunning views toward the castle. The Copper Horse statue of King George III is an imposing sight, giving you a sense of the regal history that surrounds you.
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Alexandra Gardens & The River Thames
Your walk takes you through scenic Alexandra Gardens, a favorite place for locals to relax, especially on warm days. Then, you’ll reach the mighty River Thames—famous for its role in British life, and surprisingly more pleasant than its reputation for smell suggests. Here, the views open up, and the connection between Windsor and Eton becomes obvious.
Overlooking Eton College
Across the river, you’ll see Eton College, one of the world’s most prestigious schools. It’s a site that’s often associated with British aristocracy and tradition. Your guide can share stories about the college’s history and its famous alumni, making the view more meaningful.
Thames Street and the Hidden Surprises
Walking along Thames Street, you’ll discover something unexpected in the pavement—an intriguing detail that adds a layer of curiosity. This street showcases the lively side of Windsor, blending history with modern life, shops, and cafes.
Windsor Castle and St. George’s Chapel
The tour culminates with views of Windsor Castle, the world’s largest inhabited castle and a symbol of royal continuity. While you won’t go inside, your guide will explain its architecture, history, and significance. The final stop outside St. George’s Chapel, the resting place for British monarchs, offers a poignant moment—an authentic taste of royal tradition.
What Makes This Tour Stand Out?

Knowledgeable Guides Like Eva
The reviews shine a light on how guides like Eva make this experience memorable. Beth mentions, “Eva was very knowledgeable about all things Windsor,” which is reassuring if you’re after stories that bring history to life. Expect your guide to be approachable, eager to answer questions, and to share intriguing tidbits that aren’t in books.
Stunning Views and Iconic Sights
From the sweeping vistas along the Long Walk to the detailed stories about Windsor Castle and Eton College, your eyes and mind will be kept engaged. The combination of scenic beauty and historic grandeur is just right for a leisurely walk.
Authentic, Non-Touristy Feel
Despite the popularity of Windsor, this private tour offers an intimate look away from large crowds. You’ll get personalized attention, and the stops are well-paced, giving you a real sense of the town’s character.
Cost and Value
While $171 might seem steep initially, remember that it covers a private guide and a tailored experience, making it a good value for those seeking depth and personal attention. You won’t be just another face in a large group—this is a more relaxed and detailed way to discover Windsor.
Who Is This Tour Best For?

This experience is ideal for couples, small groups, or families wanting a flexible and in-depth introduction to Windsor’s sights and stories. It’s especially suited for those with a keen interest in royal history, architecture, or local life, but also for anyone looking for a relaxed, personalized walk.
If you’re short on time but want to see the highlights and learn local insights from an engaging guide, this tour hits the spot. It’s also great for travelers who prefer walking over bus tours and value the chance to ask questions and explore at their own pace.
Price and Logistics: Good Value for a Private Tour

The $171 fee covers the entire group and lasts about 90 minutes. No need to worry about large crowds or schedules—your guide will customize the experience for your group. Meeting outside Windsor Guildhall makes it convenient and central, and the tour ends where it begins, so you can continue exploring Windsor or hop on local transportation.
Keep in mind that Windsor Castle’s entry tickets aren’t included, so if inside access is on your wish list, plan to buy those separately. The tour is best suited for independent explorers comfortable with walking and standing, and it’s a good idea to wear comfortable shoes.
Final Thoughts: Is This Tour Right for You?

If you’re looking for a relaxed, personalized way to get to know Windsor and its royal secrets, this private walking tour fits the bill. It offers a blend of scenic views, historic landmarks, and local stories, all delivered by guides who genuinely care about sharing Windsor’s character.
It’s perfect if you value quality over quantity, enjoy walking tours with a local expert, and want to avoid the hustle of larger group excursions. Whether you’re a royal enthusiast or just curious about this charming town, you’ll walk away with a deeper understanding and memorable views.
Remember, the experience’s true value lies in the detail—how your guide brings Windsor’s stories to life—and the intimate pace, allowing you to soak it all in without feeling rushed.
Frequently Asked Questions
Is the tour suitable for children?
Yes, as long as they’re comfortable walking and standing for about 1.5 hours. It’s a relaxed pace, and the sights are engaging for all ages.
Can I customize the stops?
Since it’s a private tour, your guide can tailor the experience to your interests, within the scheduled route.
Are entrance tickets to Windsor Castle included?
No, the tour covers the outside views and storytelling. Entry tickets need to be purchased separately if you wish to go inside.
What is the meeting point?
You meet outside Windsor Guildhall, a central and easy-to-find location.
How much walking is involved?
The tour lasts about 1 hour 30 minutes with stops at key sights, involving a fair amount of walking on varied surfaces.
Is the tour suitable for people with mobility issues?
It depends on individual mobility; some stops involve walking on uneven ground, but your guide can advise on accessibility.
What time of day does the tour run?
While specific times aren’t listed, most private tours are flexible and can be booked to suit your schedule.
Is the tour weather-dependent?
Yes, it’s outdoor walking, so good weather will enhance the experience. Check the forecast and dress appropriately.
What should I bring?
Comfortable shoes, a camera, and perhaps a bottle of water. The tour doesn’t include food or drinks.
Can I cancel the tour if my plans change?
Yes, cancellations are free up to 24 hours in advance, providing flexibility if your schedule shifts.
In all, this private Windsor walking tour offers a wonderful way to see the town’s highlights with personalized attention, making it a smart choice for travelers who want local insights and a relaxed pace.
Not for you? Here's more things to do in Windsor and Eton we have recnetly reviewed
- 3 Hour Private Tour of Windsor Town and Castle
- 1 Day Admission to LEGOLAND Windsor Resort
- Full Day Tour Stonehenge and Windsor
- The LEGOLAND® Windsor Resort Express from London
- LEGOLAND Windsor Resort 2 Day Admission Ticket
- Chocolatier Workshop
- Express Workshop
- Windsor and Thames Valley Bike Tour
- Mini Chocolatier Workshop
- Windsor Castle Admission Ticket
- Windsor Duck Tour: Bus and Boat Ride
