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304 North Cardinal St.
Dorchester Center, MA 02124

Discover York's hidden stories and landmarks on this engaging 75-minute tour, including a delicious chocolate tasting and lively storytelling.
Exploring York is a journey into centuries of history, charming streets, and secret corners. The Historical Gems Tour & A Taste of York Chocolate offers a lively, character-led walk that promises to unveil unseen spots and tell stories that even many locals might not know. For just over $20, this 75-minute experience packs in a surprising mix of history, humor, and a delicious chocolate treat.
What really draws us to this tour is the energetic guide, who brings York’s history to life with wit and personality. The inclusion of a handmade chocolate sample from York’s Chocolate Story adds a yummy, memorable touch — especially for those who love a sweet ending. That said, the tour is quite compact, so if you’re after an in-depth historical deep-dive, this might be more of a taste than a full course. It’s an ideal choice for travelers seeking an entertaining overview with local secrets and a fun, relaxed pace.
If you enjoy stories told with a bit of flair, love discovering hidden city gems, or are a chocolate enthusiast, this tour will hit the spot. It’s also perfect for first-timers and solo travelers, thanks to the friendly, engaging guides. However, if you’re after a longer or more comprehensive sightseeing day, you might want to supplement this with other tours or visits.

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This 75-minute walking tour kicks off at 16 Davygate, a convenient starting point in the heart of the city, just off Davygate opposite Cooplands. From there, your eccentric, energetic guide takes you through a series of carefully chosen stops that reveal both well-known landmarks and lesser-known corners. Every twist and turn is combined with lively stories, revealing York’s less obvious but equally fascinating side.
Stop 1: Starting Point at 16 Davygate
The tour begins here, where your guide — often humorously dubbed a detective or character — sets the tone for a fun, theatrical experience. Expect a warm welcome and a quick briefing before setting off.
Stop 2: Saint Helens Square
A brief 10-minute stop offers a chance to soak in the lively atmosphere and hear intriguing tales about local characters. The guide often shares amusing or surprising facts about this vibrant square.
Stop 3: Lendal
A short 5-minute walk, during which your guide points out interesting details about this historic road, often passing unnoticed by casual visitors.
Stop 4: Museum Gardens
Spanning 10 minutes, this peaceful green space hides stories behind its ancient ruins and lush grounds, making it a perfect spot for photo ops and quiet reflection. Here, expect to hear about some of the city’s historical secrets.
Stop 5: Exhibition Square
A quick 5-minute stop to hear about the city’s cultural highlights and some quirky facts about York’s architecture.
Stops 6-11: Bootham Bar, High Petergate, Stonegate, Barley Hall, Swinegate, Shambles
Each stop, lasting 5 minutes, is packed with stories, secrets, and visual delights. From the imposing entrance of Bootham Bar to the famously crooked streets of the Shambles, your guide shares anecdotes that reveal the city’s layered history.
Stop 12: Finish at Whip-Ma-Whop-Ma-Gate Sign
The final stop offers a perfect photo opportunity and a chance to reflect on what you’ve learned. The tour ends here, but the stories linger.
Hidden Gems: Your guide expertly points out overlooked treasures—concealed courtyards, unique statues, and narrow snickelways. Many reviewers, like Claudia, mention how the guide’s passion makes these ordinary sights seem extraordinary.
Stories and Secrets: From infamous characters like Guy Fawkes and Dick Turpin to lesser-known facts about York’s history, the anecdotes add depth to the city’s landscape. Reviewers like Michelle praise Sherlombo, the guide, for his amazing knowledge and humor.
Interactive and Fun: The guide often incorporates humor, puns, and theatrical flair, making history feel lively. Holly highlights that Septimus Petch made her feel included and engaged with his humor.
Chocolate Tasting: The included handmade chocolate sample from York’s Chocolate Story adds a delightful sensory experience. Reviewers like Patty love how the tasting complements the storytelling, giving a tasty taste of local craft.
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Our guides, such as the charismatic “Inspector Trinket” or Septimus Petch, are praised for their enthusiasm, knowledge, and humor. They bring York’s streets alive, sharing facts and stories with a theatrical touch.
Many reviewers mention how the guides effortlessly blend education and entertainment, making the tour suitable for a wide audience. Whether you’re a history buff, a casual visitor, or traveling solo, you’ll find the guides engaging and approachable.

At around $21.55 per person, this tour offers excellent value considering the mix of storytelling, access to hidden sights, and the chocolate treat. It’s an affordable way to gain a different perspective of York, especially if you’re short on time or prefer guided insights over solo wandering.
Timing & Group Size: The tour lasts about 75 minutes, making it easy to fit into a busy day. The reviews indicate a small, personable group environment — often just a handful of participants — which enhances the experience.
Accessibility & Weather: The tour is wheelchair accessible and runs rain or shine, so do dress appropriately for the weather. Many reviewers appreciated that the guides kept the energy high even in less-than-perfect weather.

Multiple reviews highlight the knowledgeable and engaging guides who go beyond standard sightseeing to share hidden secrets. Claudia notes how Inspector Trinket’s passion and storytelling made the tour memorable, while Michelle emphasizes how Sherlombo’s amusing narrative “brings York to life.”
Holly appreciated feeling included during the tour, and Patty loved her “day out” with the chocolate tasting. Many reviewers also mention how the tour opened their eyes to parts of York they had previously missed, making it an enriching experience.

This tour is a fantastic choice for those wanting a lively, fun introduction to York’s lesser-known stories and secret corners. It’s especially well-suited for solo travelers, first-time visitors, or anyone who appreciates humor with their history. The inclusion of a sweet chocolate sample makes it even more appealing for families or couples wanting a relaxed, engaging outing.
While it’s not a comprehensive deep dive into York’s entire history, it offers a delightful snapshot that combines entertainment, discovery, and a taste of local craftsmanship. If you prefer your sightseeing with a bit of theatrical flair, authentic stories, and a friendly vibe, this tour definitely deserves a spot on your list.
“Our Guide Inspector Trinket was passionate, very knowledgeable and entertaining!”

How long does the tour last?
The tour lasts approximately 75 minutes, with plenty of stops and stories along the way.
Where does the tour start and end?
It begins at 16 Davygate, just off Davygate opposite Cooplands, and finishes back at the same point.
Is the tour suitable for wheelchair users?
Yes, the tour is wheelchair accessible, making it inclusive for a range of guests.
What is included in the price?
Your ticket covers the guided walking tour, a lively character guide, and a handmade chocolate sample from York’s Chocolate Story.
Can I cancel my booking?
Yes, you can cancel up to 24 hours in advance for a full refund, offering flexibility for changing plans.
Is the tour in English only?
Yes, the live guide conducts the tour in English.
Are there any age restrictions?
While not explicitly stated, the tour’s lively storytelling makes it suitable for most ages, including kids and families.
What should I wear?
Dress for the weather, as the tour runs rain or shine. Comfortable shoes are recommended due to the walking involved.
Are tickets paid upfront or can I reserve and pay later?
You can reserve your spot now, and pay later, allowing flexibility with your plans.
In essence, this tour offers a lively, accessible, and uniquely engaging way to see York’s hidden sights and stories — all wrapped up with a tasty chocolate surprise. Whether you’re a history buff or just after a fun, different way to explore, this experience is well worth considering.