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Discover Portsmouth’s dark past, hidden stories, and vibrant streets on this engaging 1.5-hour Old Portsmouth walking tour led by a passionate local guide.
Exploring Portsmouth: A Deep Dive into Old Portsmouth’s Hidden Stories
Taking a guided walk through Old Portsmouth promises more than just admiring pretty streets; it’s a journey through over 900 years of history, humor, and even a touch of horror. This tour, offered by Historical Walking Tours, is highly praised for its knowledgeable guide, engaging storytelling, and authentic local insights. Whether you’re a history buff or just curious about Portsmouth’s more shadowy past, this 1.5-hour stroll offers a fascinating peek behind the city’s charming façade.
What we particularly love about this experience is the passion and local knowledge Samuel, a Portmuthian himself, brings. His relaxed yet enthusiastic style makes history lively and accessible. However, since the route involves some cobbled streets and narrow lanes, it’s worth considering if mobility is an issue. This tour suits travelers who enjoy storytelling, local culture, and discovering the stories that books often leave out — making it ideal for both history enthusiasts and casual visitors alike.

This tour is a captivating way to uncover the hidden layers of one of Hampshire’s most historic areas. Priced at just over $16 per person, it delivers a good value for those keen to explore beyond the usual tourist spots. And with a duration of about 90 minutes, it’s compact enough to fit into a busy day in Portsmouth but packed with enough stories to leave a lasting impression.
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The meeting point is conveniently located at Landport Gate, directly opposite a bus stop outside Tesco Express, about halfway down St George’s Road in Old Portsmouth. This spot sets the tone — historic, accessible, and central. You’ll end back here, making logistics simple.
From the start, Samuel’s engaging narration makes the streets come alive. He guides you through the narrow lanes and cobbled streets, revealing tales that often go unnoticed by casual passersby. His local roots shine through as he shares stories that only someone with an intimate knowledge of Portsmouth’s past could tell.
One of the highlights is uncovering why Old Portsmouth was considered so diabolical in the past. You’ll hear about the dark and sometimes humorous history of the area’s infamous characters, plus the role of pirates, rogues, and even the ‘Portsmouth Poll’ women who distracted pirates and visitors alike with their antics.
Samuel’s storytelling isn’t just about listing facts; he paints vivid pictures. For example, you might learn about Jack Nastyface, a notorious figure whose name alone sparks curiosity, or the stories behind the Blue Plaques that mark notable personalities. These plaques and historical books often omit the more scandalous or amusing stories, which Samuel happily shares.
A recurring theme is Portsmouth’s diabolical reputation. The tour explores why the city earned such a dark moniker, delving into tales of crime, espionage, and moral misadventures. For instance, the stories of coffee, espionage, and rogues entwined in Portsmouth’s past paint a vibrant picture of a city that was anything but dull.
Reviewers consistently praise Samuel for his local expertise and ability to make history accessible and fun. One reviewer called him an “excellent teacher of history” who brought Portsmouth’s streets alive, making the otherwise passing streets interesting and memorable. Others appreciated how Samuel tailor-made the experience, waiting patiently for late arrivals or adjusting the pace to suit the group.
Several reviews mention the visual appeal of the tour — from photo opportunities to just soaking in the atmosphere of Old Portsmouth. The mixture of fascinating stories and scenic streets makes for a memorable experience, especially for those interested in authentic local stories often left out of guidebooks.
More Great Tours NearbyThe tour covers approximately 1 mile, making it suitable for most. The route features some uneven cobblestone surfaces and tiny lanes, so comfortable footwear is recommended. The guide, Samuel, is wheelchair accessible, which broadens the appeal for travelers with mobility needs.
Booking is flexible, with free cancellation up to 24 hours before the tour. Plus, you can reserve your spot with no upfront payment, ideal for flexible travel plans. The tour is conducted in English, which is worth noting for non-native speakers.
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If you enjoy stories that are more than just dates and facts, this tour will resonate. It’s perfect for history lovers, families with teens, or anyone curious about the “darker” side of Portsmouth’s past. The relaxed pace and engaging guide make it suitable for those who prefer storytelling over a dry lecture.

Though relatively short, the tour’s price of around $17 per person covers a well-curated experience with a passionate local guide. You’re paying not just for the sights, but for a personal, tailored storytelling experience that brings Portsmouth’s streets to life. Many reviewers mentioned how Samuel’s enthusiasm and detailed knowledge made their visit special, even prompting repeat visits.
You’ll love the way Samuel seamlessly weaves local legends, historical facts, and amusing anecdotes. His stories reveal the city’s character — a mix of pirates, rogues, heroes, and villains. The tour doesn’t just entertain; it gives you a richer understanding of Portsmouth’s character, making your visit more meaningful.
The group sizes are manageable, allowing for questions and interaction. Reviewers appreciated Samuel’s relaxed, friendly style, making it easy to engage. Despite some unpredictable British weather, Samuel’s enthusiasm remained undampened, even waiting in the rain for latecomers.

This Old Portsmouth Historical Walking Tour stands out for its local expertise, engaging storytelling, and authentic character. It’s a fantastic choice for travelers seeking to understand the city’s more colorful past while enjoying a relaxed walk through scenic streets. The affordability combined with the depth of stories makes it a worthwhile addition to any Portsmouth trip.
Whether you’re a solo traveler, a history enthusiast, or a family with kids over 12, this tour offers a charming, eye-opening look at Portsmouth’s past. It’s especially well-suited to those who enjoy stories of pirates, rogues, and the secret histories that make Portsmouth unique. With a knowledgeable guide like Samuel, you’re sure to leave with more than just sightseeing memories, but stories that will linger long after the tour ends.
“Samuel was an excellent tour guide. We had our 12 year old son with us and it quickly became obvious that Samuel is an excellent teacher of history…”

Is the tour suitable for children?
The tour is not recommended for children under 12 years old, mainly due to the historical content and walking route.
How long does the tour last?
It lasts approximately 1.5 hours, covering about 1 mile through Old Portsmouth’s streets.
Is the tour wheelchair accessible?
Yes, the tour is wheelchair accessible, though some cobbled streets and tiny lanes may require careful navigation.
Where does the tour start and end?
It begins at Landport Gate, directly opposite the bus stop outside Tesco Express, and finishes back there.
Can I cancel my booking?
Yes, you can cancel up to 24 hours in advance for a full refund.
What should I wear?
Wear comfortable shoes suitable for walking on cobbles and uneven surfaces. Bring rain gear if the weather looks unsettled.
Are the stories suitable for non-English speakers?
The tour is conducted in English; non-English speakers might find it helpful to have some knowledge of English or bring a translator.
This tour offers a fun, authentic peek into Portsmouth’s lively, sometimes mischievous past, making it a memorable highlight for any visit to this historic city.
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