- Old Portsmouth Historical Walking Tour – an infernal den of Diabolical Demons
- Key Points
- Why You’ll Love This Tour
- A Close Look at the Itinerary
- Landport Gate: Portsmouth’s Medieval Entrance
- Spice Island: Tales of Lawlessness and Amusements
- Exploring Portsmouth’s Darker Stories
- Landmarks and Hidden Gems
- Final Stop and Revisit Ideas
- Practical Details
- Who Should Consider This Tour?
- FAQs
- Old Portsmouth Historical Walking Tour – an infernal den of Diabolical Demons
- Final thoughts
Old Portsmouth Historical Walking Tour – an infernal den of Diabolical Demons

Imagining a stroll through Portsmouth that’s a little more wicked than usual? This Old Portsmouth Historical Walking Tour promises just that—an engaging journey into the city’s less-known, more sinister stories. Perfect for history buffs, curious travelers, or anyone eager to see Portsmouth from a different angle, this tour offers a blend of local legend, medieval mysteries, and quirky landmarks.
What really caught our eye? First, the enthusiasm and knowledge of the guide—reviews rave about how engaging and humorous Samuel is. Second, the focused storytelling on Portsmouth’s darker, diabolical past, which makes history feel lively and memorable. That said, it’s a fairly short experience, about an hour and a half, so it’s best suited for those wanting a quick, intriguing peek rather than an exhaustive deep dive. If you’re up for some fun tales with a historical twist, especially with a knowledgeable guide, this could be a perfect fit.
One thing to keep in mind is that the tour includes some narrow lanes—not a problem if you’re mobile but worth noting if you’re traveling with very young children or mobility concerns. Also, the tour’s historical focus means it’s not for those looking for a family-friendly or light-hearted sightseeing experience. But for adventurous souls who enjoy stories of villains and legends, it’s a must-try.
Key Points

- Engaging and knowledgeable guides make the stories come alive.
- Short but packed with interesting content, ideal for a quick cultural fix.
- Focus on Portsmouth’s darker past adds a unique twist to the city tour.
- Accessible meeting points in Old Portsmouth make it easy to join.
- Free cancellation up to 24 hours in advance offers flexibility.
- Small group size (max 15 travelers) ensures a personal experience.
Why You’ll Love This Tour
This tour is a genuinely fun way to explore Portsmouth’s less-glamorous, more intriguing side. We loved the way the guide transformed what could have been plain history into lively, humorous stories that stick. Samuel’s passion and storytelling skills shine through, making it easier to remember the tales of villains, demons, and legendary landmarks.
For those of us who enjoy stories that aren’t just dates and facts, this tour fills the gap perfectly. It’s the kind of experience that makes history feel like a shared secret rather than a dry lecture. Plus, walking through landmarks like the medieval Round Tower and Landport Gate adds visual interest, grounding the stories in real places.
The price—around $17—may seem modest, but considering the quality of storytelling and the personal touch from a passionate guide, it offers great value. It’s a short experience, so it works well if you’re already planning a day in Portsmouth and want a taste of its more mysterious past.
A Close Look at the Itinerary

Landport Gate: Portsmouth’s Medieval Entrance
Your adventure kicks off at Landport Gate, the only original entrance of Old Portsmouth. This isn’t just a gateway—it’s where the tour begins its plunge into the city’s dark and fascinating stories. Here, your guide will reveal how Portsmouth’s origins are tied to the chapel of Thomas Becket—a surprising link that hints at the city’s medieval roots.
You’ll learn why the hot walls got their name, and why this gate is more than just stone—it’s a portal into the city’s early troubles and triumphs. One reviewer highlighted the enthusiasm of Samuel, saying he was very engaging and knowledgeable, which makes the history come alive in these narrow lanes.
Spice Island: Tales of Lawlessness and Amusements
Next, you’ll move to Spice Island, an area once known for its lawless reputation. What might seem today like a quaint part of town was once a wild, raucous scene full of dangers and joyous revelries. Our guide will share stories about why this area was considered both a hotspot for fun and a place with a frightening history—an intriguing mix that keeps the stories colorful.
Reviews note that this part of the tour reveals the myths versus the realities of the area, adding depth to the stories. The fact that the tour touches on Portsmouth’s notorious past makes it a bit edgier than your average historical walk.
Exploring Portsmouth’s Darker Stories
Throughout the tour, you’ll hear about villains, legends, and characters that brought both fear and fascination to Portsmouth’s streets over the last 900 years. From medieval beginnings to stories of villains, the guide’s storytelling makes these tales stick. One reviewer pointed out that the guide was not only knowledgeable but also very humorous, which helps in making these slightly sinister stories enjoyable rather than scary.
Landmarks and Hidden Gems
While the main focus is on stories, the stops at landmarks like the medieval Round Tower give visual anchors to the tales. You’ll get a chance to see historic sites that are often overlooked in more general tours. The tour’s small size means you’ll have plenty of chances to ask questions, and the guide can tailor the experience to your interests.
Final Stop and Revisit Ideas
The tour concludes near the Bridge Tavern, giving you a perfect spot to grab a drink or continue exploring Old Portsmouth’s charming streets. Many reviews mention that the stories make them want to revisit the city and explore further on their own.
Practical Details

The tour begins at a familiar spot—Tesco Express on St George’s Road—making it accessible from most parts of Portsmouth. It lasts about 1 hour 30 minutes, which is just enough time to enjoy a rich, story-driven experience without it becoming tiring.
Group size is limited to 15 travelers, which ensures a personalized experience and plenty of interaction with the guide. The tour is suited for most travelers who can walk comfortably through narrow lanes, and service animals and dogs on leads are welcome.
Cost-wise, at roughly $17.16, the tour offers good value considering the quality of guides and the unique stories. Flexible cancellation policies mean you can book with confidence, knowing you can cancel up to 24 hours ahead if plans change.
Who Should Consider This Tour?
This experience appeals to history enthusiasts, ghost story lovers, or anyone looking for a different way to experience Portsmouth. It’s especially suited for those who enjoy storytelling and seeing historic sites through a more colorful, less sanitized lens. If you prefer comprehensive, in-depth historical analysis, this might be a bit light—though the lively storytelling more than makes up for it. Families with older children might enjoy it, especially if they’re interested in legends and stories, but keep in mind the narrow lanes and quick pace.
FAQs

Is this tour suitable for children?
While the stories are fascinating and engaging, the focus on Portsmouth’s darker past might be better suited for older children or teens who enjoy legends and spooky tales.
How long does the tour last?
It lasts approximately 1 hour 30 minutes, making it a quick but packed experience.
Where does the tour start and end?
It begins at Tesco Express on St George’s Road and ends near the Bridge Tavern in Old Portsmouth.
Is the tour accessible by public transportation?
Yes, the meeting point is near public transit options, making it easy to join.
Can I cancel if my plans change?
Yes, you can cancel for free up to 24 hours in advance.
Are dogs allowed on the tour?
Service animals are permitted, and dogs on leads are welcome.
What makes this tour different from other Portsmouth tours?
Its focus on the city’s “diabolical” side, combined with a passionate guide who makes stories fun and memorable, sets it apart from more conventional sightseeing.
Old Portsmouth Historical Walking Tour – an infernal den of Diabolical Demons
“Samuel was a great guide, enthusiastic, interesting with immense knowledge and humorous!! Thank you!”
Final thoughts

If you’re looking for a uniquely entertaining way to explore Portsmouth’s history, especially its shadowy past, this Old Portsmouth Walking Tour ticks all the boxes. It’s a compact experience that doesn’t skimp on stories, charm, or character. With a guide who’s enthusiastic and knowledgeable, you’re more than a tourist—you become a part of Portsmouth’s history, just for an afternoon.
Ideal for those who enjoy stories with a bit of spice, this tour offers genuine value at a fair price. Just remember to wear comfy shoes, bring your curiosity, and get ready for some devilish tales that will linger long after you leave.


