Exploring Toronto with a Local: A Deep Dive into the Custom Private Walking Tour of Hidden Gems
If you’re looking to see Toronto beyond the usual tourist spots, a private, customized walking tour might be just what you need. Although we haven’t taken this specific tour ourselves, the concept of a tailored experience guided by someone who knows the city intimately can be incredibly appealing. It promises a chance to explore lesser-known neighborhoods, quirky landmarks, and local favorites that often fly under the radar.
Two aspects that immediately catch our eye are the personalization aspect—your guide crafts an itinerary based on your interests—and the flexibility of the experience, allowing for anything from a quick 3-hour stroll to an immersive 8-hour adventure. However, a possible consideration is that it’s primarily a walking experience; if you prefer a lot of transportation or to see sites from a bus or car, this might not tick all your boxes.
In general, this tour seems best suited for repeat visitors to Toronto or even locals who want to see their city from a fresh perspective. It’s also great if you love discovering offbeat places and enjoy the intimacy of a private guide rather than large group tours.
Key Points
- Customization: The tour is tailored to your personal interests after a pre-tour questionnaire.
- Local Insight: Guided by someone who calls Toronto home, offering authentic perspectives.
- Variety of Stops: From markets to beaches, quirky neighborhoods to historic landmarks.
- Flexible Duration: Choose between 3 to 8 hours based on your schedule and energy.
- Intimate Experience: Small, private group that allows for personalized attention.
- Walking Focus: Primarily a walking tour, with possible public transport as needed.
An In-Depth Look at the Toronto Custom Private Walking Tour

This tour offers a wonderful opportunity to see Toronto through a more local lens. Instead of hitting the heavily-trafficked sites like CN Tower or Ripley’s Aquarium, you’ll visit areas that are often missed by casual travelers, all curated to match your interests.
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How the Tour Works
The experience starts with a short questionnaire to understand what excites you—be it art, architecture, food, or history. Your guide then reaches out to help craft a personalized itinerary, ensuring that each stop aligns with your tastes. This level of customization makes the tour feel less like a cookie-cutter experience and more like exploring with a friend who knows the ins and outs of the city.
Throughout the day, your guide offers insider tips, historical context, and local recommendations, which significantly enriches the experience. You can choose your preferred start time and duration, making it adaptable whether you want a quick overview or a long, leisurely exploration.
Stop-by-Stop Breakdown
Hidden Home in Leslieville
The tour often kicks off with a visit to a truly one-of-a-kind residence decorated with superheroes, mermaids, Hello Kitties, and troll dolls. Curated over 20+ years by Shirley Sumaiser, this quirky home is a kind of whimsical landmark. It’s a perfect example of Toronto’s offbeat charm and provides some fun photo opportunities. According to one reviewer, “Jenn C. was so much fun and very knowledgeable about the city! She took us to several wonderful places,” highlighting how knowledgeable guides make these stops come to life.
The Cobblestone Streets of a Historic Neighborhood
Next, you might stroll through this pedestrian-only area lined with indie galleries, outdoor sculptures, and boutique shops housed in old distillery buildings. It’s a charming spot that offers a mix of history, art, and local flavor, with outdoor cafes and restaurants bustling in 19th-century architecture. One reviewer called the guide “friendly and informative,” emphasizing how these neighborhoods become more engaging with local insights.
Urban Beaches with a Quirky Twist
Relaxing at one of Toronto’s urban beaches is a highlight—white sands, pink umbrellas, and a lively waterfront vibe. It’s a favorite for those seeking a break from urban exploration without leaving the city. The views of the skyline against the water make for memorable photos, and it’s a laid-back spot to soak in the local scene.
Toronto’s Historic Market
Food lovers will appreciate a visit to a historic market established in 1803. Sampling artisanal bites and browsing local specialties here gives a sense of Toronto’s culinary roots and diverse community. The market’s long history and vibrant atmosphere make it a must-see, and guides often share fascinating facts about its evolution.
Architectural Marvels
Your guide might take you to admire a Romanesque Revival building from 1899, highlighting why it’s significant in Toronto’s architectural landscape. This stop is as much about appreciating design as it is about understanding how Toronto’s buildings tell stories of its growth and changing identity.
Rare Book Collection
Finally, you’ll get a peek into one of Canada’s most treasured rare book collections. Housed in a stunning space, this library offers a chance to explore hundreds of thousands of volumes—some available for browsing—perfect for book lovers and those curious about Toronto’s cultural fabric.
Real Experiences and Feedback
One reviewer noted, “Outstanding guide—friendly and informative—generous with his knowledge and time,” which underscores how guides often go out of their way to provide a memorable tour. Another mentioned, “We thoroughly enjoyed our 3 hours with her,” showing that even short tours can be packed with rich insights and fun discoveries.
Practical Considerations
The tour’s price of around $102.77 per person might seem steep at first glance, but considering it’s a private and personalized experience, it offers significant value—especially if you want an intimate look at the city rather than a rushed group tour. It’s also flexible: you can choose the length and start time, fitting it around your plans, which is a big plus.
Keep in mind, the tour is primarily walking, so be prepared for some steps and comfortable shoes. Public transportation may be used between sites, which could add a small cost but also helps cover more ground without tiring yourself out.
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Who Would Love This Tour?
If you’re a seasoned visitor eager to see hidden corners or a local seeking fresh perspectives, you’ll likely find this tour highly rewarding. It’s particularly suited for those who prefer a relaxed pace, want to learn from passionate guides, and enjoy discovering neighborhoods that aren’t on the usual tourist radar.
Wrapping Up: Is It Worth It?

This private, custom tour of Toronto’s hidden gems is an excellent choice for travelers craving a personalized experience. The flexibility to tailor your day, combined with knowledgeable guides who know the city inside out, creates a memorable outing that feels like exploring with a friendly local.
The stops—ranging from whimsical homes to historic markets—offer a diverse taste of Toronto’s lesser-known sides, making it perfect for repeat visitors or those who want to deepen their understanding of the city beyond the usual highlights.
While it’s primarily a walking experience, that’s also part of its charm—allowing you to soak in the atmosphere at your own pace. The price is reasonable for a private tour, especially considering the personalized approach and insider knowledge you’ll gain.
In the end, if you’re keen to see Toronto from a genuinely local perspective and love discovering quirky, offbeat places, this tour could be a highlight of your trip.
Toronto Custom Private Walking Tour of Hidden Gems with a Local
“Jenn C. was so much fun and very knowledgeable about the city ! She took us to several wonderful places . We thoroughly enjoyed our 3 hours with he…”
FAQ

How long does the tour last?
The duration is flexible, ranging from about 3 to 8 hours, depending on your preference and how much you want to explore.
Where does the tour start and end?
It starts at Roy Thomson Hall, 60 Simcoe St, Toronto, and concludes back at the same point, offering convenient access to public transportation.
Can I choose the start time?
Yes, you can select your preferred start time when booking, making it easier to fit into your schedule.
What does the tour include?
You get a private, personalized walking experience with insider tips, tailored to your interests, plus direct communication with your guide.
Are food and tickets included?
No, food, drinks, and attraction tickets are not included. It’s a walking tour, and transportation costs between sites might be extra if public transit is used.
Is this tour suitable for families or children?
While not specifically marketed as family-friendly, the focus on neighborhoods, markets, and cultural sites can be enjoyable for older children and teenagers, especially if they’re interested in exploring local culture.
What if I need to cancel?
You can cancel up to 24 hours in advance for a full refund. Cancellations made within 24 hours won’t be refunded.
All in all, this Toronto private walking tour offers a thoughtful way to peel back the layers of the city and see it through the eyes of someone who truly loves it. Perfect for those who want a slow-paced, intimate, and customizable adventure—your own personal exploration of Toronto’s hidden corners.
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