Old Portsmouth Historical Walking Tour – an infernal den of Diabolical Demons

Old Portsmouth Historical Walking Tour – an infernal den of Diabolical Demons

If you’re heading to Portsmouth and have a curiosity for the city’s lesser-known tales, this Old Portsmouth Historical Walking Tour offers a fascinating glimpse into the city’s shadowy and mischievous past. Priced at just over $17 per person, the tour lasts about an hour and a half, making it a manageable yet surprisingly rich experience. Led by a local guide whose enthusiasm and knowledge shine through, you’ll explore narrow lanes, historic landmarks, and stories that rarely make it into guidebooks.

What we love about this experience is how it combines entertaining storytelling with authentic sights—like the medieval Round Tower and the legendary Landport Gate—offering a deeper appreciation for Portsmouth’s colorful history. The tour’s small group size, capped at 15, ensures an intimate atmosphere where questions are welcome, and conversations flow freely.

A potential consideration: the narrow, winding lanes can be a bit tight and may require careful footing, especially if you’re visiting with young children or mobility challenges. Otherwise, this tour suits history buffs, fans of local legends, and anyone who enjoys stories that go beyond the usual tourist fare. It’s especially ideal if you’re interested in stories of villains, lawless areas like Spice Island, or medieval Portsmouth.

This experience made our article of 4 Best Tours In Portsmouth (With Reviews & Prices).

Key Points

• Authentic Local Guides: Guides like Samuel bring passion and humor, making history engaging and fun.
• Unique Stories & Landmarks: Learn about Portsmouth’s darker tales, including its “hot walls” and Spice Island’s lawless past.
• Compact & Manageable: The 1.5-hour tour fits well into a busy itinerary.
• Small Group Experience: Capped at 15 travelers, ensuring a personalized feel and better interaction.
• Accessible & Practical: Near public transportation, with options to suit most travelers.
• Good Value: For just over $17, you get insightful stories, memorable sights, and a taste of Portsmouth’s hidden layers.

Exploring Portsmouth’s Darker Corners

Portsmouth, often celebrated for its maritime history and historic ships, also hides stories of villains, legends, and lawless exploits. This tour takes you beyond the naval history to uncover Portsmouth’s “diabolical” side—from its medieval beginnings to its notorious Spice Island.

Landport Gate: The City’s Entrance to Darkness

The journey begins at Landport Gate, the only original entrance to Old Portsmouth. This tiny, seemingly unassuming gate opens a window into the city’s earliest days—its medieval roots and connections to Thomas Becket’s chapel. Here, the guide will highlight how this gate was once a gateway to adventure and danger alike.

One of the highlights is the story of why the “hot walls” earned their name—these medieval fortifications were meant to defend against invaders but also served as a symbol of Portsmouth’s sometimes turbulent past. As one reviewer noted, Samuel, the guide, “was enthusiastic, interesting with immense knowledge and humorous,” making even the oldest stones come alive with stories.

Spice Island: From Lawless to Leisure

The tour moves to Spice Island, an area once infamous for its dangers and lawlessness. Today, it’s a peaceful part of Portsmouth, but the stories of its past are anything but tame. You’ll hear about its reputation for fun and frolics, but also its darker history of brawls, illegal activities, and wild behaviors.

One traveler described this stop as “stunning to discover the myths and realities,” emphasizing how the stories add depth to what might seem like just another city dockyard. The guide shares fun facts and shocking tales about how this area operated in times past, giving you a vivid picture of what life was really like for sailors and locals alike.

The Experience: What to Expect

Itinerary Breakdown

• Starting Point at Tesco Express: The tour begins conveniently in central Portsmouth, making it easy to meet your guide. Here, you’ll receive your mobile ticket, and the adventure begins.
• Landport Gate: Expect a quick stop, with stories about Portsmouth’s medieval origins and its connection to Thomas Becket. This part illustrates how the city grew around its defenses and religious sites.
• Exploring the ‘Hot Walls’: Your guide will explain the nickname and history behind Portsmouth’s fortifications, giving context to the city’s strategic importance.
• Spice Island: The highlight for many is walking through this former lawless zone, hearing tales of its colorful past, and understanding how a place of chaos transformed into a vibrant part of the city.

What Makes it Special?

The tour’s real charm lies in the guide’s storytelling ability. Multiple reviews mention Samuel’s enthusiasm and humor, which make the stories memorable. His deep knowledge ensures you’re not just hearing stories, but understanding the reasons behind them. As one reviewer shared, “He was knowledgeable and enthusiastic,” making the history both accessible and entertaining.

Practical Aspects

• Duration & Timing: At 1 hour 30 minutes, it’s a perfect length for a city break, not too long to tire you out, but enough to leave you with plenty of stories.
• Small Group Size: With only 15 travelers max, the experience feels personal, allowing for questions and spontaneous conversations.
• Accessibility & Location: The start point is near public transportation, and dogs on leads are welcome, making it suitable for various travelers.

What Could Be Better?

The tour includes narrow lanes that might be tight for some, especially those with mobility issues or young children. Also, it’s weather-dependent since it’s outdoors; if the weather is poor, you might want to plan accordingly or check for rain dates.

Who Will Love This Tour?

This walking tour is perfect for visitors who enjoy stories with a bit of edge and character, especially those interested in medieval defenses, local legends, and Portsmouth’s lawless past. History buffs, curious travelers, and those who want a more authentic, less commercialized view of Portsmouth will find it especially rewarding. The small group size and enthusiastic guide create an atmosphere where questions and curiosity are encouraged.

Final Thoughts

If you’re looking for a fun, engaging, and authentic way to explore Portsmouth beyond its naval museums and classic sights, this tour offers a rare glimpse into its darker, more colorful past. Led by guides like Samuel—whose enthusiasm and humor shine through—it’s a memorable way to connect with the city’s history on a personal level.

The value is excellent for the price, considering the depth of stories and unique sights you’ll experience in just 90 minutes. Whether you’re a history lover, a fan of legends, or simply looking for a lively way to see Portsmouth, this tour hits the sweet spot of entertainment, education, and local flavor.

FAQ

How long is the tour?
The tour lasts approximately 1 hour and 30 minutes, making it a manageable and engaging experience without being overly long.

Where does the tour start and end?
It begins at Tesco Express on St George’s Road and ends at The Bridge Tavern in Old Portsmouth.

Is the tour suitable for children?
Most travelers can participate, and dogs on leads are welcome, but the narrow lanes and outdoor setting mean some caution might be needed with very young children or those with mobility issues.

How many people are in the group?
The maximum group size is 15, ensuring a friendly and personalized experience.

What should I wear?
Since it’s outdoors, comfortable shoes and weather-appropriate clothing are recommended, especially if rain is forecast.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the tour start time for a full refund.

Is the guide knowledgeable?
Absolutely. Multiple reviews praise Samuel’s knowledge, enthusiasm, and humor—making the stories engaging and easy to follow.

Are there any additional costs?
No, the stop at Landport Gate and Spice Island is free, and the tour price covers the entire experience.

In summary, this Old Portsmouth Historical Walking Tour offers an engaging way to explore the city’s lesser-known, darker stories with a lively guide in a small-group setting. It’s a fantastic choice for those wanting to see Portsmouth through a more colorful lens — perfect for history enthusiasts and curious travelers alike.