I Asked ChatGPT To Plan An Entire Day Trip In Toronto & As A Local, I'd Make A Few Tweaks

It was surprisingly smart though!

Distillery District in Toronto, Ontario: Right: Madeline in Toronto.
Associate Editor

Distillery District in Toronto, Ontario: Right: Madeline in Toronto.

The opinions expressed in this article are the author's own and do not necessarily reflect the views of Narcity Media.

ChatGPT has been all the rage lately and it seems this AI chatbot can do just about everything from planning meals to writing your resume.

But just how good is it at planning a trip? I decided to put AI to the test and see how well it knows the city of Toronto compared to a local – aka, me.

I asked ChatGPT for a detailed itinerary for a day in Toronto, including things to do, places to see, and restaurants to eat at and I was actually quite impressed with the results, although there were some things I'd tweak.

Here's what it came up with.


ChatGPT suggested starting the day off at what is probably the most iconic Toronto landmark, you guessed it — the CN Tower.

"Enjoy panoramic views of the city from the observation deck or dare to try the EdgeWalk for a thrilling hands-free walk on the tower's edge," the AI said.

I feel like this is a good place to start the day, especially if you're a tourist and haven't seen the tower before. It's one of those attractions everyone visiting Toronto should check off the bucket list, and while I certainly wouldn't be brave enough to try the Edgewalk, seeing the sweeping views from the observation deck is definitely breathtaking.

Next, it told me to "head to the St. Lawrence Market, a historic market that offers a wide range of fresh produce, gourmet foods, and unique crafts. Grab a quick breakfast or snack from one of the vendors inside."

The St. Lawrence Market is a great place to explore for locals and tourists alike. There are so many interesting vendors and goods to discover. Plus, you can get one of those famous peameal bacon sandwiches from Carousel Bakery if you're feeling hungry.

After the market, the itinerary suggested that I "take a leisurely stroll through the Distillery District, known for its charming Victorian-era buildings. Explore the art galleries, boutique shops, and coffee houses that line the streets."

The Distillery District is one of my favourite places in Toronto, so you wouldn't have to tell me twice to take a trip there. It's a must-see area in the city and, depending on when you visit, you can see some pretty cool events.

During the summer, the historic District hosts an open-air cinema called the Lavazza IncluCity Festival and you can watch movies beneath the stars. There's also a mystical Illuminarium opening soon that will make you feel like you're in a movie.

At Christmastime, the area transforms into a twinkling Winter Village with vendor cabins and a massive tree.

Lunchtime! ChatGPT told me to get a table at Cluny Bistro & Boulangerie, conveniently located in the Distillery District.

"This French-inspired restaurant offers a delightful menu with options like artisanal sandwiches, salads, and classic French dishes," it said.

While it may not have the cheapest meals, the restaurant is a popular spot to eat and has a gorgeous leafy patio, so I agree with this option.


"Make your way to the Royal Ontario Museum (ROM), Canada's largest museum of art, culture, and natural history," the platform said.

"Spend a few hours exploring the vast collection, which includes exhibits on dinosaurs, ancient civilizations, and contemporary art."

The ROM is another one of my favourite places to go in Toronto so, once more, I'm on board with this. There's always something new happening and I recently enjoyed the Wildlife Photographer of the Year exhibit. Plus, seeing dinosaur bones never gets old.

Next up, "take a short walk to the nearby Queen's Park. Enjoy the lush greenery and beautiful scenery, and take a moment to relax in this urban oasis."

I haven't actually explored Queen's Park and I think this is a nice idea, but after wandering around the CN Tower, Distillery District, and the ROM, I'm not sure if more walking is the right course of action.

I'd suggest grabbing a coffee or snack at a nearby cafe in Yorkville like Coco Espresso Bar, ZAZA Espresso Bar, or Goldstruck Coffee instead and letting your feet rest a bit.

ChatGPT then told me to go to Kensington Market, "a bohemian neighbourhood known for its diverse mix of shops, cafes, and vintage stores. Explore the colourful streets, browse through unique clothing boutiques, and pick up some souvenirs."

I think this is a good idea, but again, after already doing so much walking, I wouldn't be up to exploring the market. It would be best to choose between either the Distillery District or Kensington Market. I also feel like it would be late in the day at this point, so there may not be time to do this before dinner.

Speaking of dinner, AI suggested I sit down at "Byblos located in the Entertainment District," and I'm all for it.

"This trendy restaurant offers a modern take on Eastern Mediterranean cuisine, with dishes inspired by flavours from Lebanon, Syria, and Israel," the chatbot said.

Byblos is a Toronto staple and the food is packed with flavour. It also serves up some amazing cocktails. If you're with a group, this is a great option as it's ideal for sharing. However, if you're on your own, I'd go somewhere more geared towards individual dishes like Terroni or PAI.


With the day almost at a close, ChatGPT suggested that I "catch a performance at the historic Elgin and Winter Garden Theatre. This beautifully restored theatre hosts a variety of shows, including Broadway productions, musicals, and concerts."

The Elgin and Winter Garden Theatre is a hidden gem and, as a theatre major, I think it's a great way to end a day of exploring and relax a little. The theatre has a leafy canopy that makes you feel like you're in an enchanted forest and it's definitely worth seeing.

At this point I'd be ready to head to bed, but ChatGPT isn't done yet.

"End your evening by taking a walk along the Toronto Harbourfront. Enjoy the scenic views of Lake Ontario and the city skyline and perhaps grab a coffee or dessert from one of the waterfront cafes."

I love this thought but, again, this is way too much walking for one day. Plus, by the time the show finished, it would be quite late and many of the cafes would probably be closed. It would be best to do either the show or the Harbourfront walk (if your feet can handle it, that is)."

All in all I was impressed with how well the AI chatbot was able to put together an itinerary for a day trip in Toronto and the fact that it gave specific restaurant names was particularly cool. While some suggestions, like the CN Tower, are more geared towards tourists, I'd still enjoy doing everything on the list as a local.

The only flaw is that there are way too many activities packed into one day so, to save yourself from exhaustion, I'd only plan to go to a few of these attractions.

Before you get going, check out our Responsible Travel Guide so you can be informed, be safe, be smart, and most of all, be respectful on your adventure.

Madeline Forsyth
Associate Editor
Madeline Forsyth is an Associate Travel Editor for Narcity Media focused on Canadian and global travel and is based in Toronto, Ontario.