Historical Walking Tours Of Chester

Informative and interesting. Highly recommend!

Amazing tour. Lots of cool information laced with humour. Roland was very engaging and knowledgeable.

Super knowledgable! Funny and charming. History has never been so interesting. Loved all of Iran’s a big thank you to Roland, my fantastic guide!

I was the only visitor on this 4pm history of Chester tour. I’m not sure why, given it’s a history tour, but the guide indicated they try to keep the history portion very brief and the tone more comical, as if folks are scared or bored with any actual history. Fortunately my guide adapted himself somewhat to my interests.

Informative and fun tour with Roland, who know a lot about Chester.

Thanks Roland for an excellent tour around Chester city centre, pointing out all those extra bits that are so easy to miss plus a visit to underground Roman ruins that you would only see on a tour.

The tour guide was very well versed in the local history of Chester. ………………………………………………….. ……………………,

This was an excellent tour with Corinne, the French lady whose English was absolutely perfect (apologies if I've spelt your name incorrectly!) We learned so many interesting facts. Corinne brought the whole history of Chester to life. We used to work in a museum before retiring so this was a busman's holiday and absolutely brilliant!

Excellent funny charming information was great! Highly recommended!!

Roland was an awesome guide. He had all the information at the ready. He was friendly and engaging. We highly recommend this walking tour of Chester.

Our tour guide was Ronald (hope to spell it correctly). He was simply excellent! The tour was engaging and informative. He answered all our questions. We were lucky to see the visitors’ info centre randomly where a lovely lady told us about the tour just 5 minutes before it started. What a coincidence! Many thanks to the whole team that organizes these tours. Daniel & David (Prague, Czech Republic)

Great tour. I enjoyed my guide and the history of the area. He was very knowledgeable and shared unique bits in info about Chester! Highly recommend!

I had a great time learning a ton of fascinating facts about Chester. In the age of AI and social media, online information simply does not do justice to the city’s immense history. Huge credit goes to Roland for his engaging and humorous storytelling. Hands down, the most enjoyable part of my trip.

Rowland kept our interest with both facts and cheerful storytelling. We saw parts of Chester we might not have known were there and came to appreciate how fragile physical history of a place can be. Great way to learn about the city in an hour and get oriented to sites we might like to go back to on our own.

Chester is an amazing city and a guided tour gives you the best understanding of the city’s historical relevance and how it’s evolved. Our guide Roland was very knowledgable and passionate about the subject matter

We were the only participants but the guide did very well and was very interesting.

The tour guide was incredibly knowledgeable and enthusiastic about the history of the city of Chester. My wife and I loved all the stories and that made the history come alive. The tour highlighted so many architectural gems as well as many areas of interest that the average passerby would never know existed. Our tour guide was helpful, considerate, funny, and approachable. My wife and I highly recommend this tour for those wanting to learn more about the amazing history of Chester!

Really interesting and informative walk. Getting the many eras of Chester’s history into the experience. Roland was really knowledgeable and enthusiastic. The only improvement I would suggest is if the walk ended back where it started from.

We did the welcome to Chester walk with Roland. Amazing guide very knowledgable and enjoyable tour. Showed us things we would never have seen left to our own devices. We even got a little extra by being invited into Carbonara to look at the interior salvaged from a galleon. There were only seven of us which was nice. Everyone could hear and see. I did notice there were other groups but they were much larger (up to 30 people) must be a nightmare to hear and see everything. I would recommend you book through the tourist information at the town hall for a smaller group and ask for Roland. If you like more audience participation you can go with a Roman centurian but you will be expected to join in the marching chants etc the kids might love that one.

We booked our tour in the Tourist Information Centre. The staff were very friendly and helpful. Well… my husband and I had our guide, Roland, all to ourselves. Wow! He knew everything there was to know about Chester and more. Information just kept coming and in such an amusing and entertaining fashion. There was never a dull moment. A fantastic introduction to the city and I would highly recommend his walking tours; so suitable for all ages.

Roland was an excellent guide through the heart of Chester. Interesting facts and good pace. I would recommend this tour.

Booked through Tourist Info Centre. My husband and I had Roland to ourselves. We were thoroughly spoilt with his knowledge and enthusiasm, could have spent more hours soaking up the history. Thank you!

Roland was very knowledgeable about the history of Chester and clearly loves the city. Also made it fun with modern references too

We had a fantastic time on this tour and would recommend anyone to book! Factual, fun and interesting delivered by an expert with passion for his field making sure you go away with more knowledge than you arrived with and eager to find out more. A great experience if you've not been to the city before, as we hadn't, as it also helped us gain our bearings and enjoy the rest of our stay even more.

Lovely informative and interesting tour of Chester. Perfect timing and the guide told us lots about the history of Chester pointing out key buildings in an interesting way. Thank you

Roland was very informative and entertaining. Would definitely recommend this tour guide.

Leisurely walk around Roman walls. Very informative and interesting. Roland, our guide, possessed an exceptional knowledge of local history and made the experience lots of fun with interesting anecdotes.

We had a tour today with Roland, and it was truly a special experience. I’ve received an incredible amount of information in a very short time — exactly the kind of fast-paced, content-rich tour I love. Roland has a great sense of humor, made everything very engaging, and was clearly super involved the entire time. I’m honestly thrilled with the tour and didn’t expect it to be this amazing. I completely fell in love with the city and already want to come back again. I was also very lucky that Roland was so flexible with the route while still delivering an absolutely unforgettable experience. Thank you so much!

If you want a history tour that’s genuinely informative, well-paced, and free of gimmicks, this is the one. I had a fantastic experience on Chester History Tours with Roland as the guide. Roland is amazingly knowledgeable and has a real talent for revealing places you would normally just walk straight past without ever realising their significance. His depth of understanding of Chester is impressive, but more importantly, he knows how to share it in a way that’s engaging and accessible. The price is extremely fair. I’ve paid far more in other cities for tours that offered much less. The tour itself is also the perfect length — long enough to feel substantial, but never tiring. I did the tour on my own in March, so it was fairly quiet. Our group consisted of myself and two American ladies, and one of the unexpected highlights was how naturally we all got to know each other. Roland was very much the glue that brought the group together, and by the end we parted feeling like we’d actually made friends, not just shared a tour. What I really appreciated was the lack of gimmicks. I’ve been on plenty of tours where someone dresses up in a questionable costume that doesn’t really reflect the period they’re talking about. None of that here — just excellent storytelling and genuine expertise. Roland doesn’t limit the tour to Roman Chester (although, of course, that’s covered). He effortlessly crosses timelines, weaving in fascinating details from different eras and showing how the city has evolved over centuries. That broader perspective made the tour far more interesting and memorable. This tour is best for solo travellers, couples, groups of friends, and families with children aged 9+ who enjoy engaging storytelling, a relaxed walking pace, and learning about a city beyond its obvious highlights. Roland is clearly passionate about both history and Chester itself. He’s likeable, friendly, and extremely knowledgeable. Highly recommended.