Four Days in Toronto: Lake Surfing, Hidden Speakeasies and Coffee Galore

By Andrew Seale March 12, 2018

In 1886, Toronto mayor William Howland championed a simple, conservative ethos, calling the city “Toronto the Good." More than 130 years later the nickname lingers, yet Toronto has never been more diverse.

There's no question it's one of the most multicultural cities in the world—the BBC confirms, and how couldn't it be, given that it's growing by 100,000 new residents a year? Nothing stays the same for too long, be it a place to eat, a tucked-away cafe or a hidden indoor garden; the city has a short-term memory.

In a sense, that's what makes it an inimitable travel destination, Toronto is the whole world, a place where you can choose your own adventure and have it be different every time, but some neighbourhoods stay hotbeds for the cultural conveyor belt.

Day 1: Arrival and Kensington

If you fly into Pearson International Airport, hit the Union Pearson Express (but call it the UP, it's more Torontonian of you). Tickets are $12.35 and get you right to Union Station, Toronto's gorgeous train terminal and the key to travelling around the city. If you flew into Toronto Island airport, lucky you, you're here; hop on a quick shuttle to the city centre.

There are Airbnbs and hotels abound in the city centre, but if you're looking for a unique stay book yourself a night at one of the boutique hotels in the hip Queen Street West neighbourhood—The DrakeThe GladstoneThe Beverley, or Hotel Ocho. For a night in the city's decidedly more low-key but equally eccentric Riverside neighbourhood on Queen Street East, you can rest your head at the Broadview Hotel.

Day or night, make your way to Kensington Market by foot (Toronto is a grid and thus incredibly walkable) or via TTC streetcar (day passes are $12.50 and allow for unlimited rides, two adults can share a pass on Saturdays/Sundays and holidays).

Kensington is the epicentre of Toronto's diversity; Portuguese butchers share sidewalk space with Latin American joints hawking empanadas. It's free reign in the market and nearby Chinatown, but for a sit-down meal, you can't go wrong with Grey GardensKensington Brewing Company, La Chilaca, or Toronto's worst kept secret speakeasy Cold Tea.

Day 2: Surf check and Leslieville

Toronto's Woodbine Beach is one of the many places you can surf on the Great Lakes, which have a tendency to look like an ocean when the weather is right. Pop-by Surf the Greats in the Queen East neighbourhood for a coffee and rentals. They'll get you geared up and set up your lessons, whether it's for a stand-up paddle board overlooking the city's skyline or a wave-friendly board when the surf's up.

If surfing isn't your thing, you can rent a bike through Bike Share Toronto and head down to the trails along the waterfront or peruse the Leslieville neighbourhood, where there's no shortage of quirky shops, coffee spots, and restaurants. Your best bets? Swing by the Leslieville Pumps, a functioning gas station with an inventive kitchen, Lake Inez, in Toronto's old Chinatown, or Tabule in Riverside for new twists on Middle Eastern dishes.

Day 3: Ossington Street strip

Start on Queen Street West with a coffee from White Squirrel, named for the legendary albino squirrel (RIP) that called nearby Bellwoods park home, or grab a pastry from Nadège Patisserie across from the park. Enjoy some downtime at Bellwoods where locals congregate from spring to fall. When you're ready to hit the pavement, head west along Queen Street and north on Ossington Street, visiting the gallery spaces and fashion boutiques spaced intermittently along the route.

As dinner time rolls around, you can stay in the area and grab some classic diner poutine (cheese and gravy smothered French fries) at The Lakeview, followed by bluegrass at mainstay The Dakota Tavern. If you're feeling higher energy, head south to the King Street West stretch between Bathurst and Spadina Avenue for a sample of the myriad cocktail bars and nightlife.

Day 4: 'Toronto the Good'

What better way to cap off your visit than to play the part of the true tourist? Start on Yonge Street just south of the Queen subway stop to grab a coffee at Dineen, a historic fur shop converted into an upscale coffee spot that roasts its own beans.

Hockey fans should head to the Hockey Hall of Fame for a peek of the replica Stanley Cup. Otherwise, head up Yonge Street and west on Queen past the Eaton Centre (Toronto's behemoth shopping centre) to see old city hall, the new city hall, and Nathan Philips Square—home to the impossible-to-miss, brightly-lit Toronto sign, which makes for great Instagram fodder.

In your final hours, cut through the Eaton Centre to visit Yonge and Dundas square, a continually sprawling display of lights and signage denoting the city's commercial hub. The best part about ending your stay here: You're never more than a block away from the subway leading you directly to Union Station.

Opinions expressed are those of the author, and not necessarily those of CIBC or their partners.

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