The hotel

The Drake (rooms from £205, thedrake.ca) may look like just another designer-sexy hotel but don’t be fooled – it’s actually your keycard to the cool crowd. On vibrant Queen Street West, what was once a dosshouse (how’s that for a hipster backstory?) is now a hub of hotness with over 50 playfully luxe rooms (punchy furnishings and Malin + Goetz bath products), art installations, a basement music venue and rooftop Sky Yard bar, where cocktails and DJs rev up the scene.

The restaurant

Prime Seafood Palace (primeseafoodpalace.ca) is the baby of chef (and TV show The Bear actor) Matty Matheson. But it’s no nepo project – the excellent food is a star in its own right. Primarily a steakhouse (mains from £35), this foodie beacon on Queen Street West also applies its damn-fine touch to lobster spaghetti, tuna tartare and maple tart beneath a doorstep of brie. Special mention goes to the interiors – it’s like dining inside a wave of blonde wood.

The street

When the gelato shop – Bang Bang Ice Cream – does Boba Papa Milk Tea flavour, you know you’re in tastemaker territory. But Ossington Avenue, a regular on the world’s coolest street lists, has something for all. Try on sustainable fashion at Kotn and preloved luxe at I Miss You Vintage. Order patty melts (posh burgers) at Paris Paris and tipples at gritty-chic Sweaty Betty’s bar (below). First, though, grab that Boba Papa in an egg waffle cone and explore.

The institution

Wooden booths, vinyl banquettes, a sweep of counter and a menu that’ll have you torn between chicken ’n’ waffles and mac ’n’ cheese. So far, so regular diner. But The Lakeview on Dundas Street West isn’t any old temple of trans fats. Here since dinosaurs roamed (OK, 1932), its milkshakes et al might bring the girls and boys to its yard, but it’s the original décor that’s got Tom Cruise and John Travolta calling – Cocktail, Hairspray and were shot here.

The hangout

Once the home of booze-maker Gooderham & Worts, 150 years on, its industrial buildings are the Distillery District: aka where today’s up-for-it crowd hang. Here you’ll find walking tours: hear about Worts’s sticky end and what filthy Victorian folk did to Lake Ontario (£13, gotourscanada.com); cool boutiques; craft beer bars, and chef’s-kiss-delish Mexican food at El Catrin Destileria. Start with guacamole, made chunkily to order at your table; crickets optional.

The market

Once you’ve seen the city from 550-odd metres up the CN Tower (below), something kinder for your stomach: St Lawrence Market. As multicultural as the city itself, this foodie’s go-to – once voted the world’s best – sells everything from Ukrainian sausages to Spanish tapas via artisanal cheeses and posh dog treats. Stop for tasters, but leave room for Toronto’s peameal bacon sandwich (pork loin in cornmeal) at Carousel Bakery (£3.50).

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