In 2015, I started Roaming Historian. Our first international trip was a quick three-day trip to Toronto on the way to Montreal. This year, Roaming Historian turned ten years-old (and I was turning 50) so a return to the Toronto was necessary. Canada’s largest city feels both modern and timeless, with sleek skyscrapers standing shoulder to shoulder with Gothic churches and Victorian markets. Founded as the town of York in 1793, Toronto has grown from a small colonial outpost on Lake Ontario into one of the most diverse and dynamic cities in North America. With a mix of historic landmarks, world-class museums, bustling markets, and modern architecture, Toronto offers experiences for every traveler—and history buffs in particular will feel right at home. On our recent trip, we immersed ourselves in the city’s culture, explored its iconic attractions, and indulged in some unforgettable experiences.
Luxury at the St. Regis Toronto: A Suite and Champagne Sabering Experience
We stayed at the St. Regis Toronto, which made the trip feel like a celebration from the moment we arrived. Our Deluxe King Suite was spacious and elegant with a fireplace, separate sitting and bed room, bath and half, and great views. Jon and I were celebrating my birthday, so the butler team had a delicious slice of chocolate cake and a “Happy Birthday” banner waiting in the room when we arrived. The highlight, though, came every evening at 6 p.m., when the hotel hosts its signature champagne sabering ritual. A sommelier dramatically slices open a bottle with a saber, pouring glasses for guests. For my birthday, they dedicated the sabrage to me—an unforgettable moment that perfectly set the tone for our stay.
Things to Do in Toronto: a Perfect Itinerary
Our first big stop was the legendary St. Lawrence Market. This place has been a hub of Toronto life for over 200 years, and walking through it feels like stepping into the city’s heartbeat. The site has held a market since 1803; it also served as a meeting place for abolitionists. The location of Toronto’s first city hall, it housed the city’s prisoners in the basement. The present red-brick building (1850) hosts over 100 artisans, butchers, grocers, bakers, fish mongers, and restaurateurs. We had an amazing smoked meat sandwich from Stack’d and browsed stalls piled high with cheeses, meats, and baked goods. I couldn’t help but purchase four jars of mustard from Kozlik’s mustard (it had been used on our sandwich—did you know Canada is the world’s largest exporter of mustard seeds?).
Make sure you try the “Peameal Bacon Sandwich” at the world-famous Carousel Bakery. The quintessentially Torontonian sandwich came to be when Englishman William Davies created it using lean back bacon rolled in cornmeal. In the late 1800s, Davies became the largest pork packer in the British Empire earning Toronto the nickname “Hogtown.” Torontonians may eat the sandwich at any time of the day, including for breakfast. Served on a soft roll, the tender pork with tangy mustard tantalizes the taste buds and is a perfect treat for any meal. Its rich history (exhibits near bathrooms) and tasty treats makes St. Lawrence Market a delight. Next time, I’d love to take a St. Lawrence Market Food Tour to dig even deeper into Toronto’s history and flavors. Toronto Food Tour tickets:
Toronto has no shortage of museums, and we dove in. The Royal Ontario Museum, which opened in 1914, has some really cool exhibits. Its collections span everything from dinosaurs to ancient Chinese temples, reminding visitors that Toronto is one of the most cosmopolitan cities on earth. If you want to see how history, art, and culture intersect in one place, the ROM delivers. Royal Ontario Museum Tickets
We also visited Casa Loma, Toronto’s very own Gothic Revival castle that makes you think you’ve stumbled upon a set for a Disney movie or the estate of a European monarch. Built in the early 20th century by financier Sir Henry Pellatt, the castle’s soaring towers (you can climb up in them), grand halls, lavish interiors, and secret passageways make you feel like you’ve been whisked to Europe without leaving Ontario. Sir Henry Pellatt’s former home is 200,000 square feet of stunning architecture and décor. From the stately library to the elegant dining room, opulence is seen throughout. I was a child when Casa Loma first enchanted me and I’ve been going back ever since. It’s quite a ways out though, so you might want to consider a “Hop-on/Hop-Off Bus” to take you to around downtown Toronto. City Sightseeing
Throughout all of Toronto I feel like I’m on a high, but to literally be on one then you should zip up the highspeed elevators to the top of the CN Tower. When it was built in 1976, it held the title of the tallest freestanding structure in the world—an honor it held for decades. The views from the top are breathtaking—you can see the city stretching north and, on clear days, all the way to Niagara.
Next door is Ripley’s Aquarium, where we delighted in seeing lots of marine life. The sharks were a huge attraction, but the playful rays thrilled me, too. I had learned my lesson last time I visited that the “Dangerous Lagoon,” a moving sidewalk taking you through a tube where sharks, rays, fish, and turtles swim around you should be savored as slowly as that sidewalk moves. We gave it plenty of time and just took in the wonders around us.
Canada’s national pastime (they’ve been playing the game since the 1800s) is celebrated in style at the Hockey Hall of Fame. Whether you’re a diehard fan or a casual observer, interactive exhibits, legendary memorabilia, and the Stanley Cup make this attraction unforgettable. I’m not an avid hockey-lover but I’ve been there twice now and enjoyed both times. I love seeing the vault for the Stanley Cup (the building was the former Bank of Montreal 1886) and I’ve also enjoyed seeing how gear has changed throughout the decades. Hockey Hall of Fame Tickets:
Walking Through History
One of my favorite ways to soak in a city’s personality and past is simply walking. I wandered past St. James Anglican Church (gorgeous neo-Gothic gem dating from 1800s) past St. Lawrence Market and down to the water front one day. On another, I strolled past Old City Hall with its Romanesque-Revival style to the playful Toronto sign at Nathan Phillips Square. A downtown walking tour would be a great way to add stories and historical context to the city’s already striking architecture. A guide brings the stories behind the architecture to life—how this colonial town grew into the vibrant, multicultural city it is today. I’ve done one before and had fun. Here are some ideas for Toronto walking tours:
Downtown Toronto Historic Walking Tour
Toronto Distillery District Walking Tour
Toronto Discovery District 2 hour Walking Tour
Toronto’s Kensington and Chinatown Walk
Cheering on the Chicago Cubs (er…Toronto Blue Jays)
Jon is a life-long Cubs fan, so when we found out that his favorite team would be playing in Toronto while we were there, I booked the tickets. The Rogers Centre opened in 1989 as the SkyDome, it was the first stadium in the world with a fully retractable roof. Watching baseball beneath the shadow of the CN Tower was a neat experience. Even though the Cubs lost, I enjoyed a hot dog, a game, and a bunch of happy Blue Jays fans around us.
Dining Delights
Toronto is a foodie’s dream with a dining scene as diverse as its people. We had good meals at:
- Terroni Adelaide—an Italian restaurant housed in a former courthouse (1853). You pass former jail cells on the way to the bathroom and the public square out back was where hangings occurred. Jon and I ate here in 2015 and it was as good—if not better—than we remembered. I had the “tonnarelli alla norcina” and it was sublime.
- Joey King St.—modern, stylish, and delicious. They had nice happy hour specials and the truffle fries were amazing.
- Cactus Club Café—great flavors with even better views. Service left a lot to be desired, but the chicken did not.
- Chop Steakhouse—fair prices for steak, but it came with a wait.
What I Would Like to Do Next Time I’m in Toronto
A Kensington Market Food Tour sounds really cool. Kensington is one of Toronto’s most eclectic neighborhoods, known for its immigrant roots, vibrant murals, and irresistible food. A tour here lets you taste dishes from around the world while learning how each community helped shape the Toronto we know today. Tickets:
For something a little quirkier, the Bata Shoe Museum tells history through footwear—yes, shoes! From Indigenous moccasins to Marilyn Monroe’s stilettos, every pair has a story. I’ve heard great things about this attraction, so next time I’m going to try to stop by. I’ve been to the Ferragamo Museum in Florence, Italy many times and am always stunned at how much history can be learned through fashion. Bata Shoe Museum Tickets
To see Toronto from a different angle, I recommend a Sightseeing Harbor Cruise—there’s nothing like gliding across the water with the skyline unfolding before you. The Toronto Islands have long provided locals with a breezy escape, and gliding across the water gives you the same sense of perspective that 19th-century ferry passengers must have felt, watching a young city rise along the shoreline. 60-minute Sightseeing Harbor Cruise Tickets
What always strikes me about Toronto is how seamlessly its past and present are intertwined. You’ll find glass skyscrapers rising beside Victorian churches, bustling markets that have fed generations, and cultural institutions that rival the best in the world. For some other fun Toronto sites, see my previous blogs where I talk about: Mackenzie House, the Distillery District, Steamwhistle Brewery, Corktown, Enoch Turner Schoolhouse, Little Trinity Church, and more. I hope you enjoy Toronto as much as we do. As you can see, I’m already mentally planning for a return trip. I hope we don’t wait ten years like this visiting gap.
What’s your favorite part of the city?
Happy travels!
Toronto Tours and Tickets:
Royal Ontario Museum Tickets: https://www.viator.com/tours/Toronto/Royal-Ontario-Museum-Ticket/d623-17145P1?pid=P00161535&mcid=42383&medium=link
Toronto Hockey Hall of Fame: https://www.viator.com/tours/Toronto/Hockey-Hall-of-Fame/d623-33848P1?pid=P00161535&mcid=42383&medium=link
Bata Shoe Museum Tickets: https://www.viator.com/tours/Toronto/Bata-Shoe-Museum-Admission/d623-69732P1?pid=P00161535&mcid=42383&medium=link
Toronto Sightseeing Harbor Cruise: https://www.viator.com/tours/Toronto/Toronto-Harbour-Sightseeing-Cruise/d623-5868CRUISE?pid=P00161535&mcid=42383&medium=link
Secret Toronto Food Tour with St. Lawerence Market: https://www.viator.com/tours/Toronto/Secret-Food-Tours-Toronto/d623-7812P37?pid=P00161535&mcid=42383&medium=link
Taste the World in Kensington Market Toronto Food Tour: https://www.viator.com/tours/Toronto/Toronto-Food-Tour-Kensington-Market-Sweets/d623-5918KENSINGTON?pid=P00161535&mcid=42383&medium=link
Downtown Toronto Historic Walking Tour: https://www.viator.com/tours/Toronto/Toronto-Historic-Downtown-Walking-Tour/d623-5579015P2?pid=P00161535&mcid=42383&medium=link
Toronto Distillery District Walking Tour: https://www.viator.com/tours/Toronto/Toronto-Distillery-District-Walking-Tour/d623-5597P2?pid=P00161535&mcid=42383&medium=link
Toronto Discovery District 2 hour Walking Tour: https://www.viator.com/tours/Toronto/Tips-Based-Bike-Tour-of-Toronto/d623-108104P7?pid=P00161535&mcid=42383&medium=link
Toronto’s Kensington and Chinatown Walk: https://www.viator.com/tours/Toronto/Small-Group-Walking-Tour-of-Torontos-Kensington-Market-and-Chinatown/d623-6934KENCHI?pid=P00161535&mcid=42383&medium=link
Toronto Hop On Hop Off Sightseeing Bus: https://www.viator.com/tours/Toronto/City-Sightseeing-Toronto-Hop-On-Hop-Off-Tour/d623-5694P21?pid=P00161535&mcid=42383&medium=link
Amy French, Ph.D., is the voice behind Roaming Historian. A professional historian and seasoned traveler, she shares stories that blend history and travel to give readers a deeper understanding of the places they explore.
Distillery District
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