The Inside Out Guide to Toronto

Toronto city guide
Credit: Miguel Romero

Toronto, Canada’s largest city, is perhaps best known for its musical exports—Drake, Shawn Mendes, and The Weeknd, amongst others. But there’s a lot more to the city. It’s also home to the 2019 NBA Champions, the Toronto Raptors (a major source of local pride), and a near endless selection of standout dining, cultural, and sightseeing options.

The city, which has a population of 2.8 million residents as of 2016 (the most recent Census count), is also incredibly diverse. Almost half of Toronto residents are foreign-born, making it second globally (after 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, that impressive diversity is reflected in the array of dining options throughout the city in 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. So, if you’re planning a trip North anytime soon, ahead, a few recommendations for where to stay, eat and drink, sightsee, and get tattooed in the bustling Canadian metropolis.

Where to Get Tattooed in Toronto

Inside Out Toronto: Our very own tattoo studio right in the heart of downtown Toronto is home to resident artists Curt Montgomery—whose signature bold, minimal style has led him to tattoo the likes of Halsey, Joe Jonas, and Sophie Turner—and Alex Abbey. The shop also includes a regular, rotating lineup of guest artists including folks like Mira Mariah—Ariana Grande’s go-to tattooer—and Insta-famous South Korean artist Goodmorning. 379 Queen Street W., Entertainment District

Ink & Water Tattoo: Artists and co-founders Prairie Koo and Michael Pecherle started this chic studio basically by accident while working on other projects. 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. 2063 Yonge St., 2nd Fl., Midtown; 1303 Bloor St. W., Brockton Village

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 suburb of Toronto—over a decade ago. Hu is best known for his riffs on Asian motifs, with plenty of dragon designs in his tattoo portfolio, but the team at the popular studios (there are four Chronic Ink locations across the GTA [Greater Toronto Area]) are capable of a wide array of styles, from minimal line work to watercolor. Plus, they do lots of custom work, too. 252 Eglinton Ave. E., Midtown; 378 Yonge St., Downtown

Private studios: There are a ton of great private tattoo studios across the city that are home to some of Toronto’s most talented artists including Twin Oaks Tattoo, led by owner and resident artist Linsday April; Always Tattoo, a new female-run studio on St. Clair West co-owned by hand poke tattoo artists Kate Memphis and Odette Beja; and the yet unnamed East-end studio run by Jess Chen, an artist who specializes in large-scale nature-inspired tattoos.

Where to Stay in Toronto

The Broadview Hotel: A cool boutique hotel, The Broadview opened up in the city’s East End in 2017. The building’s former tenant, Jilly’s Strip Club, shuttered in 2014, but cheeky nods to its salacious past are included throughout the hotel’s design, like brass poles subtly incorporated into the space (repurposed as shelving, for example) and thick red velvet curtains. The rooms come tricked out with record players and in-room vinyl libraries, and other hip touches include a French press for DIY caffeine satiation and ultra-modern marble-filled bathrooms. Rates typically range from $178 to $300 per night. Plus, there’s a rooftop bar with a small plates menu, popular for mingling and ogling the skyline views. Nearby, outdoors enthusiasts will also appreciate the five-minute walk to the Don Valley hiking and biking trail. 106 Broadview Ave., Riverside

The Drake Hotel: 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 19 room apartment-building-turned-hotel, 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 super compact utilitarian digs for a brief solo visit to spacious suites.

Another benefit of this space? There’s no need to stress over planning evening outings while staying here. Choose between DJs spinning on the hotel’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. Another hip amenity: a ‘pleasure menu’ of saucy toys and accessories from local sex shop Come As You Are, delivered room service-style. 1150 W. Queen St., Queen Street West

The Annex Hotel: Nestled in the heart of The Annex—the West-end Toronto neighborhood for which the hotel is named—this relatively new space is a modern take on the hotel experience. How so? It’s a no-nonsense hotel that’s run digitally with online check-in and staff that you can text for help. The Annex Hotel was designed to be simple; a place to crash after days and nights spent exploring the city. Every room offers plenty of natural light and is decked out with local artists’ work. The hotel also includes a café so you can satisfy your morning coffee craving that transforms into a wine bar every day at 4pm. Rooms start at $190 per night. 296 Brunswick Ave., The Annex

Bisha Hotel & Residences: If you’re looking for something a little more upscale, this sleek hotel in the Entertainment District is a top contender. The glossy black and white decor in the rooms is accented by music and pop art paraphernalia and vibrant geometric patterned carpeting. There’s also an entire floor of Lenny Kravitz-conceived suites outfitted by the musician’s interiors firm, Kravitz Design. Prices begin at $270 per night. 80 Blue Jays Way, Entertainment District

What to Do in Toronto

Toronto Islands: If you’re visiting Toronto during the warmer months and want a different vantage point of the city, a brief respite from a bustling downtown core, and an excuse to take a ferry ride, consider spending an afternoon hopping around the Toronto Islands. The area is comprised of three connected islands: Centre, Ward’s, and Algonquin. There’s plenty of parkland to explore, a boardwalk overlooking Lake Ontario, and, of course, great vistas of the city. Ferries run every half hour and it’s an approximately 10-minute journey each way. Looking for an alternate route? You can also rent a kayak and paddle your way to the islands where you can enjoy its beaches, the Centreville Amusement Park, and plenty of perfect picnic spots.

Kensington Market: This market has its roots in the 1920s, when the predominantly Jewish residents of the area would set up shop in front of their homes—the colorful Victorian-era buildings that still line the streets today—to sell their goods to one another. Now, in that same spirit, if you walk through Kensington Market you’ll find an incredibly diverse selection of shops and restaurants—everything from clothing stores to hole-in-the-wall pancake, bagel, and taco joints. And the area really comes to life during the summer when Kensington goes car-free on the last Sunday of the month and the streets are taken over by shoppers and street performers.

Distillery District: Over the past two decades, the Distillery Historic District has experienced a renaissance as a cultural destination. Spread over 13 acres, the revitalized neighborhood comprised of 47 buildings—some dating as far back as the 1850s—is considered to be North America’s largest collection of Victorian industrial architecture. These days, it’s a quaint pedestrian-only area with a range of shopping and dining options, working artists’ studios, 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. And if you’re in town during the holiday season, check out the Toronto Christmas Market—a festive takeover of the Distillery District complete with boozy hot chocolate, carollers, and a massive 50-foot Christmas tree.

Explore Ravines Galore: Toronto 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 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; instead, you’ll have to hit the streets to check it out. Head to Graffiti Alley, 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 between Spadina Ave. and Portland St., Queen Street West

Art Gallery of Ontario (AGO): The AGO, which first opened its doors in 1911, is one of the largest art museums in North America. Its collection consists of over 95,000 works that span from 100 CE to present day, including a vast assortment of Canadian and Indigenous artwork. The museum’s current exhibitions include a collection of politically satirical art from 1800 to today, and a Yayoi Kusama Infinity Mirrored room. Another great perk? Anyone aged 25 or younger gets in free. 317 Dundas St. W., Downtown

Bata Shoe Museum: Yes, this really is a museum devoted to shoes. So. Many. Shoes. The unique institution opened in 1995, stemming from (and named for) shoe industry executive Sonja Bata’s sprawling private footwear collection. There are a lot of distinctive pairs to ogle since Bata’s 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, which opened in September 2018. 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—2017’s I Hear She’s A Real Bitch—about her own experiences in the business. 892 Queen St W., Trinity-Bellwoods

Richmond Station: A refreshingly mellow 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. Heinrich opened Richmond Station in 2012, and has been helping evolve the city’s downtown financial district dining scene ever since. For a relative bargain, opt for the $45 prix-fixe lunch, which consists of three courses (including a selection of four different appetizers for the table). 1 Richmond St W., Old Toronto

Mother’s Dumplings: There are six Chinatowns in the Greater Toronto Area, which means ample options for getting some great dumplings, hand-pulled noodles, dim sum, and more. 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, including lots of familiar staples like pork buns, a range of dumplings (as the spot’s name touts), and scallion pancakes. 421 Spadina Ave., Chinatown

Sneaky Dee’s: This Toronto institution is a must-visit the first time you’re in the city. Head there for a night of music, nachos and beer. The restaurant-meets-bar-meets-music-venue first opened in 1987, before moving to its current location in 1990. ‘Sneaks’ as it’s locally known, operates within two floors at the corner of College and Bathurst Street and has held tight to its musical roots. Over the past 30 years musicians of all sorts—from more notable acts like Arcade Fire and Feist to student grunge bands—have graced the Sneak’s stage. 431 College St., Harbord Village

Related: More Inside Out City Guides

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