After years of guiding travelers through every alley, mural, and coffee shop this city hides, I’ve heard a lot of questions. Some make me laugh. Some make perfect sense. But the ones that get you closer to understanding Toronto are rarely the first that pop into a visitor’s head. Here’s the fun part. I’ll tell you both: what tourists usually ask, and what I think they should ask if they want a deeper taste of the city.
“Where’s the Best Place to Take a Photo?”
Every tour group asks this within the first ten minutes. And yes, Graffiti Alley (Rush Lane) is iconic for photos- vibrant murals, constantly evolving street art and even influencer shoots happen there all day long. It’s pretty much the unofficial outdoor gallery of Toronto’s urban art scene. But what you should ask is: “Which wall here tells a story I won’t see online?” Because some pieces in Graffiti Alley and in Kensington Market’s side alleys capture neighborhood history, community voices, or commentary on city life that photos alone will not explain. Peel back the surface and you will notice references to heritage, activism, and even local music culture that you would miss between selfies.
“Is Kensington Market Worth Visiting?”
The short answer most travelers want is yes or no. Here’s the thing. Kensington Market is worth it! It is this endlessly colorful mashup of cultures, food, vintage shops, murals, musicians and boho personality. It has been a multicultural destination for generations, where you will find everything from Caribbean jerk chicken and Mexican tacos to indie coffee houses and thrift boutiques. But instead of asking “Is it worth it?” ask: “What makes Kensington Market feel like Toronto?” When you ask that, you will hear about how the streets spill out with Spanish, Italian, Portuguese and Caribbean groceries. You will learn how a place becomes a neighborhood because its people shape it, not because it is on a list. Pedestrian Sundays turn the whole area into a living festival of locals and visitors celebrating street art, music and pop-ups.
“Is Toronto Safe?”
Totally reasonable question. Toronto is generally considered safe for visitors, but like any big city, there are pockets where you want to stay aware of your surroundings, especially late at night or in quieter areas. Do not flaunt valuables, keep your belongings close, and trust your instinct if something feels off. But a much better question is: “Where do locals feel comfortable exploring after dark?” Ask that, and I will tell you about places like Trinity Bellwoods Park for a sunset picnic crowd, West Queen West for indie galleries and evening drinks, or the cozy cafés that stay open late into the evening. Those spots give you a sense of how Torontonians live, rather than how they tourist.
“What Should I Eat in Toronto?”
People often want the biggest, most famous meal, where the best steak or brunch is. But food in Toronto is not about one signature dish. This city’s culinary personality is its global blend. You will find amazing meals in classic spots, but the real magic is hidden in everyday places with stories. So instead, ask: “What neighborhood snacks are locals obsessed with?” Then I can tell you to try a butter tart from a small bakery in Kensington, a Caribbean roti from a tiny shop on Baldwin Street, or a late-night banh mi that the neighbourhood regulars swear by. Those bites say more about Toronto’s culture than any brochure recommendation ever will.
“Do People Here Actually Use Public Transit?”
Yes. Toronto’s streetcar, bus, and subway system (TTC) is how most locals get around day to day. It is not glamorous, but it is authentic. But what visitors usually want to know is, is it easy to use? Which is fine. But I prefer the question: “What’s the weirdest transit moment you have seen?” That lets me tell you about turning down a conversation mid-ride because someone recognized my accent, or watching a busker start a drum circle by Yonge Street on a Saturday afternoon. Those are local vibes, not logistics.
“What Neighborhood Should I Visit Next?”
People often point to the big names: Distillery District, Harbourfront, or the CN Tower. Great places. Not wrong. But the better questions are: “Where do creatives live, eat, and hang out?” Then we dive into West Queen West, named one of the coolest neighborhoods in the world with galleries, indie boutiques, and jazz bars. Or we talk about Leslieville’s Sunday farmers’ market and craft coffee scene. Those are not just stops on a map. They are communities.
The Question That Changes Everything
If you save one question for the end of your visit, let it be this: “What part of Toronto feels most alive on a random Tuesday, without any plans?” Because that is the heart of this city. It is the lane where the mural sprouted overnight. It is the alley with a busker on a beatbox groove. It is the cafe where the barista remembers your name by day two. Toronto is not about monuments. It is about moments. And the best questions always lead you into them.