Windsor is a fantastic place for walking tours—its compact, easily navigable streets are lined with royal history, charming shops, and scenic riverside views. Whether you’re drawn to exploring Windsor Castle’s grandeur, wandering through Eton’s historic college town, or uncovering some of the town’s darker legends, there’s a tour that matches your curiosity. We particularly like the Windsor Town Daily Walking Tour for its lively storytelling and insider knowledge, and the Windsor: Private Dark Side Walking Tour for those interested in the town’s ghostly tales that make history feel a little more alive (or perhaps, a little more eerie). If you want a quick, insider glimpse that combines local tips with efficient sightseeing, the Windsor: Express Walk with a Local is also a smart choice.
Quick Overview
In this guide, we cover four of the best walking tours in Windsor, each offering a different way to experience the town. From guided group adventures to private explorations, these tours provide insights into Windsor’s royal past, spooky stories, and local life. For detailed information on each, keep reading—each tour offers unique highlights and experiences that suit different interests and schedules.
1. Windsor Town Daily Walking Tour (11am & 2pm)
At number 1, the Windsor Town Daily Walking Tour is a popular choice, with a solid 4.7-star rating based on 71 reviews. This 1.5-hour stroll offers a well-rounded introduction to Windsor, perfect for first-time visitors or those short on time. The tour departs twice daily, at 11am and 2pm, from Windsor Guildhall, and it’s led by a knowledgeable local guide who shares engaging stories about Windsor’s royal connections and historical sites.
Highlights include Windsor Castle, which has been the royal family’s official residence for over 900 years, and Eton College, where you can imagine Prince William and Prince Harry walking the same halls. The guide takes you on The Long Walk, a stunning 2.5-mile avenue lined with ancient trees that lead directly to Windsor Castle, making this one of the most iconic views in the town. Walking down Broad Street and admiring the Victorian architecture around Victoria Square adds to the sense of stepping back in time. Guests rave about the guide’s enthusiasm and local stories, with one reviewer noting, “It was very informative and interesting. Our guide was very pleasant and we thoroughly enjoyed it.”
Bottom Line: If you want a concise, engaging introduction to Windsor’s key sights with friendly storytelling, this tour is tough to beat. It’s especially good for history lovers and those eager to get their bearings quickly.
2. Private Guide (Walking Tour of Windsor & Eton)
Number 2 on our list offers an exclusive experience perfect for those who prefer personalized attention. The Private Guide (Walking Tour of Windsor & Eton) lasts about 2 hours and is ideal for families or small groups seeking a tailored exploration. This tour covers the main sights—Windsor Castle, Eton College—and delves into the stories behind the buildings and characters that shaped this area.
What makes this tour stand out is the flexibility and custom approach. Your guide, who has been praised for their passion and deep knowledge, can adjust the focus based on your interests—whether that’s Royal history, local legends, or hidden corners. One reviewer mentions, “Kip was very knowledgeable and knew the area well,” and highlights how the tour helped them learn about Windsor’s past in a relaxed setting.
You’ll stroll around the town, stopping at points like Windsor Castle and Eton College, learning about their historical significance and royal connections. The tour is a great option if you want a more intimate experience with a local expert who can answer all your questions.
Bottom Line: For travelers who want a personalized, flexible walking experience with in-depth stories on Windsor and Eton’s history, this private tour offers excellent value and insider insights.
3. Windsor: Private Dark Side Walking Tour
If you’re intrigued by ghost stories and the darker side of Windsor, the Windsor: Private Dark Side Walking Tour is a must. This 1.5-hour adventure explores Windsor’s spooky legends, haunted buildings, and eerie tales from a knowledgeable guide. Rated 5/5 by two reviewers, it’s the top choice for thrill-seekers and those curious about Windsor’s ghostly reputation.
Your guide will take you through the streets where you can learn about the most haunted building in England and hear about sightings of the Windsor Witches, the Ghost of Queen Victoria, and other chilling legends. The tour also covers the history behind Windsor’s ghost stories, including sightings of phantom figures and eerie legends that have persisted for centuries. One reviewer describes it as, “The whole group loved this tour. With a wonderful storyteller and guide, we saw parts of Windsor we would never have seen if it wasn’t for this tour.”
This tour is perfect for those who enjoy history with a spooky twist, and it provides a different perspective on Windsor’s past—one that’s definitely more mysterious and spine-tingling.
Bottom Line: If you like stories of hauntings and ghostly legends, this tour offers an entertaining and eerie way to experience Windsor’s darker side.
4. Windsor: Express Walk with a Local
For travelers short on time but eager to see Windsor through local eyes, the Windsor: Express Walk with a Local fits the bill. This 1-hour tour is ideal for those who want a quick yet authentic look at Windsor’s major landmarks and vibrant street life. With a maximum group size of 8, you’ll get a more personal experience, visiting sites like Windsor Eton Bridge, Alexandra Gardens, Windsor Royal Station, and the famous Long Walk.
The guide shares tips on the best local pubs, cafes, and spots to get a good meal or a coffee—useful if you’re planning to explore more on your own after the walk. Reviews highlight how this tour maximizes your time and provides a fresh, local perspective. One traveler said, “Discover Windsor from an insider’s point of view in just an hour, hitting all the best spots.”
This tour is especially suited for those with limited time or for travelers who prefer a relaxed, informal stroll with practical tips for the rest of their visit.
Bottom Line: A great choice for a quick, local-focused introduction to Windsor, especially if you want insider tips and efficient sightseeing.
$107 per person
How to Choose the Right Windsor Walking Tour
When selecting a walking tour, consider what interests you most. Do you want a rundown with plenty of stories? The Windsor Town Daily Walking Tour offers terrific value for its duration. If your priority is a personalized experience, the Private Guide tour will give you tailored insights. For those fascinated by ghost stories, the Dark Side Tour delivers spooky legends in a short, engaging format. And if you’re pressed for time but still want to see the highlights, the Express Walk with a local offers a quick taste of Windsor’s charm.
Booking early is advisable, especially in peak summer months and on weekends. Check the availability and start times to align with your itinerary, and consider combining a longer tour with a visit to Windsor Castle or Eton College for a fuller experience.
Windsor has a variety of walking tours perfect for different interests and schedules. Whether you’re a history buff, a ghost story enthusiast, or just want a quick local fix, these options will help you make the most of your visit. For a comprehensive, friendly introduction, the Windsor Town Daily Walking Tour is hard to beat. If you prefer a more intimate or themed adventure, the private or dark side tours offer memorable experiences. And for those on a tight schedule, the Express Walk provides a quick, authentic Windsor experience.
Whatever your choice, booking ahead will ensure you don’t miss out on these enriching walks through Windsor’s streets and stories.