The Inside Out Guide to Toronto

Toronto city guide
Credit: Miguel Romero

Toronto, Ontario’s capital, is the largest Canadian city, and one of the largest cities in North America, unique among big cities for its slew of interconnected, distinctive neighborhoods, with plenty of standout dining, cultural, and sightseeing options to explore. With a population of 2.8 million residents as of 2016, the most recent Census count, it’s also incredibly diverse: almost half of Toronto residents are foreign-born, making it second globally to only Miami in terms of a city’s proportion of foreign-born residents; and, since there’s no dominant cultural or nationality among Toronto’s immigrant population, there’s truly impressive diversity, reflected in the array of dining options throughout the city (and cultural enclaves like Chinatown, Little India, Greektown, and Little Jamaica). Easily reachable from NYC via several affordable flights that are just an hour a half long, it’s a great long weekend destination from the Northeast. Ahead, a few choices for where to stay, eat and drink, sightsee, and get inked in the bustling Canadian metropolis.

Where to Get Tattooed in Toronto

Ink & Water Tattoo: Artists and co-founders Prairie Koo (who also goes by Mr. Koo) and Michael Pecherle started this chic studio basically by accident while working on other projects; Pecherle describes their foray into tattoo artistry as “having fun exploring a new art form.” The team of artists at Ink & Water’s two locations work with lots of first-time clients, which makes sense given the spot’s clean, inviting, and, yes, very Instagram-friendly aesthetic. That means tons of white, some greenery, and neon signage, for a vaguely cool, Millennial catnip sort of vibe that could just as easily be a hip matcha cafe or nail spot. It’s been praised for its female-friendly feel and is certainly a refreshing, more inviting departure from the look of most tattoo studios. 2063 Yonge St., 2nd Fl., Midtown; 1303 Bloor St. W., Brockton Village

Black Line Studio: Another Toronto ink spot that’s a welcome contrast to the typical appearance of a tattoo studio, Black Line Studio is nicely appointed space with an open, airy layout and lots of wood trim. In addition to getting inked, the space also offers piercings, laser removal, body jewelry, and there’s even a skincare boutique and art gallery on-site. There’s an uptown location of Black Line as well. 573 King St. W., Fashion District

Chronic Ink: Co-founded by tattoo artist Tony Hu and his business partner, Tristen Zheng, Chronic Ink started at a Chinese mall in Markham, a ‘burb of Toronto, over a decade ago. Hu is best known for his riffs on Asian motifs, with plenty of dragons making cameos in his designs, but the team at the popular spots are capable of a wide array of styles, and does lots of custom work, too. 252 Eglinton Ave. E., Midtown

Where to Stay in Toronto

The Broadview Hotel: A cool boutique hotel housed in a long-running former strip club, in an increasingly gentrified ‘hood, The Broadview Hotel opened up in the East End’s Riverside area in 2017. The handsome circa-1891 Romanesque revival building’s former tenant, Jilly’s Strip Club, shuttered in 2014, but cheeky nods to its salacious past are included throughout The Broadview’s design, like brass poles subtly incorporated into the space (repurposed as shelving, for example) and thick red velvet curtains, while the fanciful wallpaper in the lobby bar is a reproduction of the building’s original wallpaper style, dating back over a century, found many layers beneath. The rooms come tricked out with record players and in-room vinyl libraries; other hip touches include a French press for DIY caffeine satiation and ultra-modern, clean, marble-filled bathrooms. Rates tend to range from $178 to $300 per night. There’s also a rooftop bar with a small plates menu, popular for mingling and ogling the skyline views that’s glass-encased for enjoying in cooler temps, and a great alfresco pick in warmer weather. Nearby, outdoors enthusiasts will appreciate the five-minute walk to Don Valley hiking and biking trail. 106 Broadview Ave., Riverside

The Drake Hotel: If this hip hotel feels like a cooler, kitted-out version of a real home, no surprise there: The Drake’s 19 rooms occupy a former apartment building, evidenced by exposed brick and granite flooring. Colorful touches complement the spot’s historical, homey elements, like bright murals, vintage stereos and colorful low-slung mid-century furnishings, as well as ample, rotating collection of art on display. Fitting right into its location in the vibrant Queen Street West neighborhood, The Drake, which opened in 2004, has become a hub of Toronto art, design, and food. You’ll feel the energy the moment you walk into the former apartment building, where original granite floors, exposed brick, and other historical touches live alongside vivid murals, green leather seating, vintage stereos, and pieces from a rotating art collection.  

Rooms start at $172 per night, and come in a range of sizes, from really compact, utilitarian digs for a brief solo visit to spacious suites. There’s no need to stress over planning evening outings while staying here: choose between DJs spinning on the property’s rooftop or the Drake Underground, the hotel’s subterranean performance space, which hosts live music, poetry slams, karaoke nights, and more. The next morning, tuck into one of the city’s best brunches at the onsite eponymous restaurant, where the eclectic weekend brunch menu includes buckwheat crepes with gravlax, a green shakshuka, and gumbo. And you can sweat it out in style, too: in lieu of a sad, fluorescent-lit fitness center with an ancient elliptical, a loud treadmill, and some mismatched free weights, guests at The Drake are offered free yoga and spin classes at nearby boutique studios. Another hip amenity: “a pleasure menu” of saucy toys and accessories from local feminist, ethical, anti-capitalist sex shop Come As You Are, delivered room service-style. 1150 W. Queen St., Queen Street West neighborhood

The Ivy at Verity: This European-style boutique hotel is smack in the middle of the city, located in what was once an 1850s chocolate factory. Looking for something super-private, pretty romantic, and far more intimate than what a behemoth, high rise chain hotel can offer? Consider The Ivy at Verity, a boutique option that strives to replicate small, indie European counterparts. It’s got an ultra-central location, is housed in a former 1850s chocolate factory, and is named for nearby private women’s club, Verity. There are just four rooms on offer here, all with luxe touches like Italian linens and soaking tubs, while the fresh blooms throughout the property are arranged by The Ivy’s in-house florist. This is no cookie-cutter hospitality experience here: Each room has its own distinctive vibe, with differing color palettes (i.e. gilded, with velveteen walls; teal, trimmed with crisp white). Prices start at $240 per night. The Ivy at Verity’s prime address is walking distance from historic Corktown, the Distillery District (more on that in a moment), as well as St. Lawrence Market, an iconic market space dating back two centuries, where prepared and fresh food vendors are open Tuesdays through Saturdays, with a more extensive farmer’s market on Saturdays, and antiques market on Sundays. 111d E. Queen St., Old Toronto neighborhood

Bisha Hotel & Residences: This sleek, luxurious property is located inside a 44-story high rise (with hotel rooms as well as apartments) in the Entertainment District, decked out with a velvet and marble-lined lobby. It’s actually part of Loews’ portfolio, but Bisha looks decidedly more indie and edgy, perhaps thanks to its creator, Charles Khabouth, the idiosyncratic Lebanese-Canadian hospitality heavyweight and CEO of Ink Entertainment, which runs over 15 restaurants, as well as a slew of bars and nightclubs, and even music festivals. As far as the rooms go, the glossy black and white decor is accented by music and pop art paraphernalia and vibrant geometric patterned carpeting. Or, there’s an entire floor of Lenny Kravitz-conceived suites, with spacious digs outfitted by the rocker’s interiors firm, Kravitz Design. Be sure to keep an eye out for the art on display, which could include, say, a Warhol print; the works are sourced from the hotel’s own  3,000-piece collection. Prices begin at $270 per night. 80 Blue Jays Way, Entertainment District

What to Do in Toronto

Distillery District: Over the past two decades, the pedestrian-friendly Distillery Historic District has experienced a renaissance as a cultural destination, spread over 13 acres. The revitalized ‘hood, comprised of 47 buildings, some dating back as far as the 1850s, that once housed whiskey-focused spirits company Gooderham & Worts, is considered to be North America’s largest collection of Victorian industrial architecture. These days, it’s a quaint, cobblestone-lined, pedestrian-only area worth exploring, with a range of shopping and dining options, working artists’ studios, and various art galleries, and more. In pursuit of a boozy activity that nods to the area’s name and onetime ? Hit up the original, Distillery District-born, namesake location of Mill Street Brewery: It was established in 2002 as East Toronto’s first new commercial microbrewery in over a century. Another nearby hops purveyor to visit is Steam Whistle Brewing, and for sake fans, check out Ontario Spring Water Sake Company.

Toronto Islands: For a different vantage point on Toronto, a brief respite from city life, and an excuse to take a brief boat ride, spend an afternoon on Toronto Islands, comprised of three connected islands, Centre, Ward’s, and Algonquin. There’s plenty of parkland to explore, a boardwalk overlooking Lake Ontario to stroll down, and, of course, great vistas of the city. Ferries run every half hour; it’s an approximately 10-minute journey in order to get some peaceful island time, but if you’re visiting in the winter, note that the Ward’s Island terminal is the only Toronto Islands stop open year-round. Warm weather activities include beaches, the Centreville Amusement Park, and plenty of perfect picnic spots, while wintertime pursuits include cross country skiing or ice skating.     

Explore Ravines Galore: The city is home to the world’s largest network of ravines, a patchwork of parkland winding throughout the city, some of it densely forested, other parts more groomed, with a diverse range of conditions, from wetland areas to hardwood filled forests. The ravines occupy 20% of Toronto’s layout, and have even earned the city a nickname: “the city within a park.” A sizable portion of the city’s extensive ravines are on private property, but a vast 45,000 acres worth of ravines are on public land, available for hiking, jogging, biking, or walking dogs. Two ravine walks to try: Cedarvale Park and Ravine, off the Eglinton West subway stop, and Rosedale Ravine, off the St. Clair subway stop.

Where to Get Inspired in Toronto

Graffiti Alley: Some of Toronto’s most interesting art isn’t found in a posh gallery or major museum: you’ll have to hit the streets to check it out. Head to Graffiti Alley, aka a two-block stretch of Rush Lane, between Spadina Ave. and Portland St., near Queen Street West. That’s where you’ll find the most extensive range of the city’s plentiful street art on display. Expect an array of styles and themes, an explosion of bright hues and an exciting mishmash of graphics, text treatments, and messages both silly and serious. Rush Lane btwn. Spadina Ave. and Portland St., Queen Street West

Bata Shoe Museum: Yes, this really is a museum devoted to shoes. So many shoes. This unique institution opened in 1995, stemming from (and named for) shoe industry executive Sonja Bata’s sprawling private collection. Bata’s footwear fanaticism was spurred by more than her professional path: she traveled frequently, finding many of the kicks and other accessories in her collection in all corners of the world. There are a lot of distinctive pairs to ogle: her permanent collection encompasses nearly 13,000 items, and there are also special exhibits focusing on specific designers (i.e. Manolo Blahnik) or historical themes, like “Want: Desire, Design and Depression Era Footwear,” open through March 30, 2020. The space is stylish, too, a sleek, angular structure designed by architect Raymond Moriyama. 327 Bloor Street West, Old Toronto

Where to Eat and Drink in Toronto

Le Swan: Toronto restaurateur Jen Agg is behind this French diner concept, opened September 2018 in the former space of Swan. Expect a mix of French bistro classics like steak frites, salade niçoise, and French onion soup, served alongside familiar American comfort fare, like meatloaf with mashed potatoes and chicken fried steak. Agg has been a key figure in Toronto’s culinary scene for over a decade, and wrote a frank tell-all about her own experiences in the business, including all sorts of sexist situations, in 2017’s I Hear She’s A Real Bitch. Also worth checking out? Agg’s other restaurants that are currently open, including the elegant wine bar/restaurant Grey Gardens she co-opened in 2017 with Momofuku alum Mitch Bates in the Kensington Market area, and Rhum Corner, which serves up Haitian cocktails and fare, like frozen piña coladas, oxtail, and fried plantains. 892 Queen St W., Trinity-Bellwoods

Mother’s Dumplings: In a city with six Chinatowns in the greater Toronto area, there are many options in various directions for getting some great dumplings, hand-pulled noodles, dim sum favorites, roast duck, and more around Toronto. One highlight in Toronto’s main Chinatown, located west of Old Toronto, is Mother’s Dumplings, which opened in 2005 and relocated to this larger space in 2010. The Northeastern Chinese fare uses recipes that owner and chef Zhen Feng learned from her mother in Shenyang, China, with lots of familiar staples like pork buns, a range of dumplings (as the spot’s name touts), and scallion pancakes. 421 Spadina Ave., Chinatown

Richmond Station: A refreshingly mellow, but no less devoted, take on farm to table fare is the M.O. at Richmond Station. Co-owner Carl Heinrich, who won season 2 of Top Chef Canada, helms a kitchen that uses largely local ingredients and does a lot of in-house handiwork, including baking, fermenting, and curing. Richmond Station also does much of its own butchering: the restaurant is known to solely buy whole animals, resulting in unique uses of offal ingredients employed in specials. Heinrich opened Richmond Station in 2012, and has been helping evolve city’s downtown financial district dining scene since. For a relative bargain, opt for the $45 prix-fixe lunch, which includes three courses, with four different appetizers for sharing in the mix for even more variety, which they dub “snacks for the table,” like beef tartare and wild leek pierogi croquettes. 1 Richmond St W., Old Toronto

Edulis: This romantic tasting menu spot run by husband-wife team Michael Caballo and Tobey Nemet serves up a constantly refreshed range of courses in a snug, candlelit setting. By tasting menu standards, it’s certainly a bargain, as five courses are priced at $65, and seven courses go for $90 per person. The Mediterranean and Spanish-inflected menu changes daily, is seafood-heavy and comprised of one set selection of courses; it could involve fluke sashimi, roasted skate, or lamb served three ways (roast leg, braised shoulder, and sausage). Seasonal supplements are impressive, too: they might include black or white truffles, Chantecler chickens baked in hay, spot prawns, or dry aged Berkshire pork. 169 Niagara St, King West Village

Related: More Inside Out City Guides

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