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Jetsetter Guides

72 Hours in Ontario

It's Canada's most populous province—and one of its largest (four times the size of the United Kingdom). Charlotte Steinway spent 72 hours exploring Ontario's varied landscape and shares her tips for taking in all its best features, from the tree-lined shores of Lake Muskoka to Toronto's chic sips and sleeps.

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With a lounge offering complimentary WiFi, almonds and cappuccinos, Porter Air is undoubtedly the most civilized way to arrive in Toronto, Ontario’s cosmopolitan capital city. Daily flights from Boston, Chicago, Newark and Washington D.C. will land you in Billy Bishop Toronto City Airport, located on an island 1.5 miles from downtown Toronto, just a five-minute (and free) ferry ride away.

Once you’ve arrived on the mainland, it’s time to check in. Hotel options run the gamut from the hipster-centric Drake hotel to the condo-style Cosmopolitan. Scene seekers love the Thompson Toronto for its rooftop infinity pool, while families and business travelers love the Westin Harbour Castle for its downtown location and panoramic Lake Ontario views.

Spend the afternoon exploring Leslieville, the hip east side neighborhood flanked with vintage shops, restaurants and creative agencies dotted along Queen Street East. Start with brunch at Lady Marmalade, the Toronto outpost of the wildly popular Victoria restaurant with the same name. The salad and sandwich options are divine but the killer benedicts trump all — try the “cochinita pibil” variety, which comes with their signature hollandaise atop Yucatecan pulled pork and citrus-marinated onions.

After lunch, grab a flat white at Te Aro and take to the street — Queen East, that is. Shop refurbed Midcentury Modern designs at GUFF, girlie rockabilly garb at Doll Factory By Damzels, funky tailored menswear at Studio We and designer consignment at Here & Now.

Head to Luma in the entertainment district for dinner, the city’s best spot for celeb spotting during Toronto International Film Festival. The Oliver & Bonacini-run restaurant is located in the festival’s hub, TIFF Bell Lightbox, and serves up modern Canadian staples like braised rabbit cavatelli and Northern Woods mushrooms paired with an impressive wine list.

Partygoers should head to west for craft beer in a casual setting at Thirsty & Miserable in the funky Kensington Market, or live music at Bovine Sex Club in West Queen West. Nearby, sample the molecular mixology at BarChef — the Sailor’s Mojito is made with Sailor Jerry rum, vanilla air and “beach essence.”


Grab an early breakfast at the Senator, the retro diner that’s been doling out excellent challah French toast and house-smoked lox to the Downtown Core since 1929.

Next, it’s on to Muskoka, the sprawling lake two hours north of Toronto by car or bus that’s considered Canada’s answer to the Hamptons. Just don’t call them the Muskokas — locals say it’s the easiest way to spot a newbie. And while we’re at it, avoid the terms “lake house” and “cabin.” In Ontario, they’re called “cottages,” regardless of size or scale. Meaning Tom Hanks, Goldie Hawn and Steven Spielberg all have (multi-million dollar) cottages in the area. How quaint.

First stop on the way to Cottage Country is Weber’s, on Highway 11. It’s been a favorite pitstop since 1963; their famous cheeseburgers, poutine and chocolate milkshakes are an enduringly popular summertime obsession. Enjoy lunch on one of the colorful backyard picnic tables, or inside a vintage train car-turned-dining-area (several of these are "parked" along the property).

Rather than rent a cottage for the weekend, shack up at the fully-equipped J.W. Marriott the Rosseau Muskoka Resort & Spa. With four pools, five restaurants and bars, a topnotch spa and Adirondack chairs galore, the resort has prime real estate overlooking Lake Rosseau, the body of water just north of Lake Muskoka.

Observe the area’s best scenery with a sunset dinner cruise on one of the Muskoka Steamships, which depart from Muskoka Wharf and offer gorgeous views of the lake’s islands, inlets and tree-lined shores.


Start the day with a butter tart — a raisin- or pecan-filled Canadian delicacy — from Don’s in Bala before heading out to Muskoka Outfitters in Bracebridge. There, you’ll have the option of renting a kayak or standup paddleboard, or partaking in a guided cycling tour or hiking excursion.

Reward your adventurous spirit with a seasonal, locally-sourced lunch at Riverwalk, whose Mediterranean-styled dining room overlooks the waterfalls of the Muskoka River. The market-driven menu changes regularly here, but expect dishes like house-made wild mushroom pâté and braised Ontario lamb shank, followed by an inventive selection of homemade ice creams.

Next, it’s on to the local libations. Knock back some tastings of Muskoka Brewery’s famous Mad Tom IPA and Cream Ales before a brewery tour, given at 1:30, 2:30 and 3:30pm every Thursday to Saturday. Afterwards, stop by Muskoka Lakes Winery to sample their signature cranberry wines, crafted from Ontario cranberries, blueberries and raspberries.

Later, repair to the hotel for a treatment at the Spa Rosseau (the relaxation pool overlooks the hotel pools and lake), or head to the lakefront for canoeing, kayaking, and water trampoline-ing. Finish the night off with a charcuterie plate, oysters and customizable flatbreads at Teca, the J.W. Marriott’s sultry ground floor Italian restaurant. And then it might be time to call it a night—depends on when your flight is the next morning.



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