Forget the standard tourist trail. To experience the true pulse of contemporary Toronto, you need to dive into its vibrant, creative neighbourhoods. This is a city where a former dosshouse becomes a design hotel epicentre, where a celebrity chef's restaurant stands on its own culinary merit, and where a historic distillery now houses the city's most stylish crowd. Here's your insider's guide to navigating the cool.
Designer Digs and Culinary Stars on Queen Street West
At the heart of the action lies Queen Street West, a bustling artery of creativity. Here, The Drake Hotel (rooms from £205) has transformed from its humble origins into a cultural hub. Don't let its sleek, designer-sexy facade fool you; this is your passport to the local scene. With over 50 playfully luxurious rooms featuring punchy furnishings and Malin + Goetz bath products, it's far more than a place to sleep. The hotel pulses with energy, hosting art installations, a basement music venue, and the rooftop Sky Yard bar, where cocktails and DJs define the evening mood.
Just steps away, a major foodie beacon shines. Prime Seafood Palace is the creation of chef and The Bear actor Matty Matheson. This is no mere vanity project. The restaurant has earned its stellar reputation, serving as a premier steakhouse with mains from £35 while also excelling at dishes like lobster spaghetti and tuna tartare. Save room for the decadent maple tart beneath a doorstep of brie. The experience is heightened by stunning interiors that wrap diners in a wave of blonde wood.
Ossington Avenue: A Global Cool Street Contender
A short journey north leads to Ossington Avenue, a strip regularly featured on lists of the world's coolest streets. The vibe here is immediately established by spots like Bang Bang Ice Cream, where innovative flavours like Boba Papa Milk Tea served in an egg waffle cone confirm you're in tastemaker territory. The avenue caters to diverse tastes, offering sustainable fashion at Kotn, pre-loved luxury at I Miss You Vintage, and exceptional dining. Indulge in patty melts (posh burgers) at Paris Paris or sample inventive tipples at the gritty-chic Sweaty Betty's bar.
Historic Hangouts and Market Treasures
Toronto's charm lies in its blend of the new and the nostalgically enduring. The Lakeview on Dundas Street West, a diner operating since 1932, is a prime example. While its menu of chicken 'n' waffles and milkshakes draws crowds, its original décor has attracted Hollywood. It served as a filming location for movies like Cocktail and Hairspray, earning calls from stars like Tom Cruise and John Travolta.
For a taste of the city's industrial past repurposed for modern leisure, head to the Distillery District. Once the home of the Gooderham & Worts distillery, its Victorian industrial buildings now house a pedestrian-only village of cool boutiques, craft beer bars, and acclaimed restaurants. Take a walking tour to hear about the district's history (from £13), then settle in for chef's-kiss-delicious Mexican food at El Catrin Destileria, where guacamole is made chunky and fresh at your table.
No Toronto visit is complete without a trip to the iconic St Lawrence Market. As multicultural as the city itself, this food hall—once voted the world's best—is a feast for the senses. Vendors sell everything from Ukrainian sausages and Spanish tapas to artisanal cheeses. Be sure to leave room for a true Toronto classic: the peameal bacon sandwich (pork loin in cornmeal) from Carousel Bakery for around £3.50. It's the perfect, hearty end to a exploration of Canada's most dynamic city.
