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Discover Portsmouth’s darker past on this 1.5-hour historical walking tour, led by passionate guides exploring diabolical tales and landmark sites for just $17.16.
Get ready to explore the lesser-known, darker side of Portsmouth with the Old Portsmouth Historical Walking Tour. Priced at $17.16 per person, this 1 hour 30 minutes tour offers a captivating look at the city’s diabolical legends, villains, and mysterious characters spanning over 900 years of history. Led by a local guide with a deep love for Portsmouth’s stories, the tour ensures an engaging experience packed with fun facts and hidden tales that often escape the guidebooks.
This tour is ideal for those who enjoy a bit of intrigue, history, and lively storytelling. It begins at Tesco Express on St George’s Road and ends at The Bridge Tavern in Old Portsmouth. With most bookings made 33 days in advance, it offers flexible timing options, making it easy to fit into a day of sightseeing. While the tour involves walking through narrow lanes and historic sites, it’s accessible for most travelers, including those with service animals or dogs on leads.


The tour kicks off at Landport Gate, the only remaining original entrance to old Portsmouth. This historic gate invites curiosity as the guide explains its significance in the city’s medieval history and its connection to Thomas Becket’s chapel. Visitors learn about Portsmouth’s ‘hot walls’, which earned their name from their historical role in defending the city.
The Landport Gate stop is brief but packed with stories about its origins, setting the tone for tales of intrigue and villainy that follow. Visitors get a glimpse of the medieval roots of Portsmouth and how these structures relate to its early defenses.
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Next, the tour moves to Spice Island, a location known for lawless revelries and mythical stories. Here, the guide reveals the frightening and shocking history behind what has become a lively hub today. This spot was once notorious for its dangers and amusements, blending stories of fun and frolics with darker tales of lawlessness.
The 10-minute stop at Spice Island allows for a closer look at its mythical legends and real stories, offering a contrast between its current vibrancy and its troubled past. Visitors can imagine the chaos and mischief that once characterized this part of Portsmouth.

Landmarks like the medieval Round Tower feature prominently in the tour. The guide highlights this iconic structure, explaining its historical importance and how it relates to the city’s defenses. It’s a key stop that offers architectural insights and a chance to appreciate Portsmouth’s ancient fortifications.
This site encapsulates the blend of history and legend that pervades the tour, making it a favorite for those interested in military history and medieval architecture.

The tour also discusses Portsmouth’s ‘open-air’ church, a unique feature that reflects the city’s religious and social history. The guide shares stories about the church’s medieval beginnings and its role in the community through the centuries.
This stop underscores how Portsmouth’s spiritual sites intertwine with its history of villains and demons, adding depth to the overall narrative of the city’s dark past.

At Portsmouth Point, the tour delves into the myths versus realities of this lawless area. Known historically for dangers and entertainments, the guide reveals the shocking history behind the lively streets.
Visitors learn about the stories of mischief, villains, and hotspots of chaos that shaped this part of the city, providing context to Portsmouth’s reputation as a hotbed of lawlessness in its earlier days.
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This tour offers multiple time options to suit your Portsmouth itinerary. Whether morning or afternoon, the flexible scheduling makes it easy to incorporate into a busy day of sightseeing or leisure.
The meeting point at Tesco Express is conveniently located, and the tour wraps up at the historic Bridge Tavern in Old Portsmouth, perfect for further exploration or a relaxing drink afterward.
With a maximum of 15 travelers, the tour maintains an intimate and engaging atmosphere. This smaller size allows for better interaction with the guide and more personalized storytelling.
The tour is accessible for most travelers, with service animals allowed and dogs on leads welcome. Some lanes are narrow, which is worth considering for those with mobility concerns, but overall, it suits a wide range of visitors.

Guided by Samuel, a passionate local with immense knowledge and a humorous approach, this tour has earned consistent praise. Reviewers frequently mention his enthusiasm, depth of knowledge, and ability to make history fun.
Samuel’s storytelling makes the dark tales of Portsmouth lively and memorable, keeping participants engaged throughout the 90-minute walk. His clear language even appeals to international visitors, including French speakers, who appreciate his accessible English.
Most bookings are made about a month in advance, reflecting its popularity. The tour offers free cancellation up to 24 hours before the scheduled start, providing flexibility for changing plans.
Weather can affect the experience; if canceled due to poor weather, participants are offered a full refund or a reschedule. Since the tour is primarily walking, comfortable shoes and weather-appropriate clothing are recommended.
This Old Portsmouth Historical Walking Tour stands out for its focus on the darker, more intriguing stories of the city. It offers a rich narrative that merges history, legend, and local lore, all delivered with enthusiasm and humor by a passionate guide.
The stops at Landport Gate, Spice Island, and the medieval Round Tower are highlights that bring Portsmouth’s villainous past into vivid detail. The tour’s small group size ensures a personal and engaging experience, perfect for those interested in lesser-known history and hidden tales.
While the 1.5-hour duration makes it a manageable stroll, be prepared for some walking through narrow lanes and historic streets. It’s an excellent choice for history buffs, local enthusiasts, or anyone keen to uncover Portsmouth’s diabolical legends.
“Samuel was a great guide, enthusiastic, interesting with immense knowledge and humorous!! Thank you!”
How long is the tour?
The Old Portsmouth Historical Walking Tour lasts approximately 90 minutes.
What is the price?
Tickets cost $17.16 per person, making it an affordable way to explore Portsmouth’s lesser-known history.
Where does the tour start?
It begins at Tesco Express on St George’s Road and finishes at The Bridge Tavern in Old Portsmouth.
Is the tour suitable for children or pets?
Yes, service animals are allowed, and dogs on leads are welcome. The tour is generally suitable for most travelers, but some narrow lanes may require caution.
What kind of stories are shared?
The guide emphasizes villains, villainous legends, and diabolical tales from Portsmouth’s 900-year history.
Can I cancel my booking?
Yes, free cancellation is available up to 24 hours before the tour start time.
Are there different tour times available?
Yes, the tour offers a selection of times to fit your schedule.
Is the tour accessible?
The tour accommodates most travelers, with consideration for narrow lanes and walking distances.
What do past participants say?
Reviews consistently praise the enthusiasm, knowledge, and humor of the guide, Samuel, who makes history fun and engaging.
Is this tour suitable for international visitors?
Absolutely, as the guide speaks clearly and accessibly, making the stories understandable for non-native English speakers.
What should I wear?
Since weather can vary, wear comfortable shoes and prepare for outdoor walking conditions.
This Old Portsmouth Historical Walking Tour offers a lively, informative look into the city’s darker past, guided by a passionate local who makes history come alive. It’s a great choice for those eager to uncover hidden legends and explore Portsmouth’s more mischievous side.