Toronto’s icons are easy to spot. The CN Tower dominates the skyline, red streetcars weave through downtown, and Fairmont Royal York has stood proudly across from Union Station for nearly a century. But according to Fairmont Royal York concierge Monika Grossenbacher, the city’s most memorable experiences often happen beyond the postcard moments.
As part of Now Toronto’s Concierge Diaries series, Grossenbacher has crafted the ultimate extended-weekend itinerary for visitors who want to experience both the Toronto everyone knows and the one only locals talk about, featuring a healthy balance of exclusive neighbourhood discoveries and hidden gems with must-see landmarks.
“It always depends on the guest’s interests, their mobility and time constraints and budget, and whether or not they are first time visitors or have children,” Grossenbacher explained. “But assuming they’re open to anything, I’d try to give them a mix of local and casual, and extravagant and exclusive.”
Begin with Toronto luxury at its finest
A stay starts with checking into the Fairmont Gold floor, the hotel’s elevated “hotel within a hotel” experience. Guests enjoy a private reception, exclusive lounge complete with fireplace, complimentary refreshments throughout the day, and a peaceful retreat above the bustle of downtown.
After breakfast in the Fairmont Gold Lounge, Grossenbacher’s itinerary skips the usual crowds in favour of something few visitors ever experience: an exclusive private morning tour of the Royal Ontario Museum before it opens to the public.
From there, guests can tailor the morning depending on their interests. History lovers can head to Queen’s Park to watch Ontario’s Legislative Assembly from the public gallery when House meetings are in session, while shoppers can browse the boutiques lining Yorkville Village.
Discover one of Toronto’s most underrated lunches
Rather than recommending one of the city’s buzziest restaurants, Grossenbacher points visitors toward one of her favourite hidden culinary gems.
Lunch takes place at Gallery Grill inside the University of Toronto’s historic Hart House, an elegant dining room tucked inside one of the city’s most beautiful collegiate buildings.
Afterward, wander next door into the Thomas Fisher Rare Book Library, home to one of the world’s largest collections of rare books and manuscripts. Even visitors who aren’t literary enthusiasts are often struck by the library’s dramatic architecture.
Before leaving Yorkville, Grossenbacher recommends creating something to remember the trip by.
At Kandl Artistique, guests can design their own custom-scented candle, leaving with a handcrafted souvenir that’s far more personal than anything found in a gift shop.
Now onto dinner, where the gears shift entirely.
Instead of a fancy dining room, the evening ends at Sunny’s Chinese, tucked into the heart of Kensington Market, one of Toronto’s most vibrant neighbourhoods.
Experience Toronto beyond the skyline
The second day begins just steps from the hotel at Stratus, a hidden breakfast spot perched on the 36th floor of the Toronto-Dominion Centre.
After breakfast, Grossenbacher leads guests through Toronto’s sprawling PATH network toward the Jack Layton Ferry Terminal. Along the way, they’ll pass one of downtown’s hidden Banksy works — a surprise many visitors never know exists.
The destination is Ward’s Island.
While many visitors hop off the ferry, snap a skyline photo and leave, Grossenbacher recommends spending time exploring the island community itself through a guided walking experience. Its quiet cottages, winding pathways and lakefront scenery feel worlds away from downtown despite sitting only minutes across the harbour.
“It’s one of Toronto’s most unique and idyllic communities,” she said.
Meet the makers shaping modern Toronto
Back on shore, lunch awaits at Waterworks Food Hall before an afternoon exploring West Queen West, one of Toronto’s creative hubs.
Rather than shopping for souvenirs, Grossenbacher encourages visitors to make one.
At Ratelier, guests can participate in a fragrance workshop and leave with a custom perfume unique to their Toronto visit.
The evening continues west with dinner at Chinese-Jamaican inspired spot Patois before returning downtown for cocktails/mocktails at Library Bar inside the Fairmont.
For those wanting another iconic Toronto neighbourhood, the Distillery District also earns Grossenbacher’s recommendation. Beyond its preserved Victorian industrial buildings and cobblestone streets, visitors can explore local businesses like Spirit of York, which blends Toronto’s history with its evolving food and drink scene.
See Toronto from behind the scenes
On the final morning, Grossenbacher swaps luxury transportation for something many locals rely on every day: Bike Share Toronto.
The brief ride leads to Morning After in CityPlace, known for its colourful, camera-ready brunches.
From there, it’s time for another experience most visitors never realize exists.
At Ripley’s Aquarium of Canada, guests can participate in a private turtle feeding before exploring the rest of the country’s largest aquarium — an exclusive experience that can only be offered through concierge.
The VIP treatment continues next door at Rogers Centre with a behind-the-scenes stadium tour, including access to the Blue Jays clubhouse, luxury suites and spaces normally closed to the public.
Back at Fairmont Royal York, in the Fairmont Gold Lounge, guests have time to refresh before one final evening out.
Dinner is reserved at Akin, where the multi-course blind tasting menu transforms each course into a surprise.
To end the weekend, Grossenbacher offers two equally memorable options: cocktails at Bar Cart on The Esplanade or an evening of live jazz at Reservoir Lounge.
Toronto’s icons are only the beginning
If visitors only have 24 hours, Grossenbacher simplifies the experience without sacrificing what makes Toronto special.
She recommends starting with a peameal bacon sandwich at Paddington’s Pump inside St. Lawrence Market before boarding the city’s hop-on, hop-off sightseeing bus to experience Toronto’s biggest landmarks. Depending on the visitor’s interests, the evening could include a neighbourhood food tour, live theatre in the Entertainment District, a Blue Jays game, or a twilight bicycle ride through the Toronto Islands.
But regardless of how long someone stays, Grossenbacher believes Toronto reveals itself best through its neighbourhoods.
Whether it’s discovering the peaceful waterfront at Ireland Park, admiring the soaring glass galleria at Brookfield Place, finding skyline views from Riverdale Park, or simply wandering streets filled with restaurants representing nearly every corner of the world, the city’s personality comes alive far beyond its biggest attractions.
“I hope you’ll join us again,” Grossenbacher said. “Because there’s still so much more to explore in Toronto.”
To unlock more Toronto, read our Concierge Diaries series, powered by Destination Toronto.
