Toronto: Where to Stay, What to Eat, and What to Do

Toronto City Guide
The Anndore House Hotel
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The Anndore House Hotel

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It’s known for its CN Tower, unhinged politicians, the Maple Leafs, Raptors, and the illustrious beard of one Aubrey Drake Graham. In size and structure, Toronto looks a lot like any-big-city-U.S.A. Look a little closer though, and you’ll notice the streets are clean and the people, noticeably courteous, are all from — everywhere. Coming from the Midwest, this multiethnic culture is what I love most about Toronto. Scores of languages are tossed around on the streets. Hair is textured, plated, waved, and rolled a million different ways. You can travel the world by standing in one spot.

This is perhaps my fifth visit, but the first in six years. Some of my fondest memories involve tables, tequila, Toronto, and the absolute best and most gorgeous girlfriends in the world. One of the latter has finally decided to give up the thug life for marriage. I dropped everything to be there and see the end of an era with my own eyes.

Here I detail where you’ll want to stay, eat, and what you’ll want to do with a few days in T.O.

Toronto Travel Guide

Crew Love: Flying Porter Airlines

Porter Airlines

Porter Airlines is a lesson in the importance of personality. Their planes may be small and loud, but their staff knows the meaning of hospitality. They are polite, smiley, and accommodating. My favorite part of flying Porter may actually be their in-flight magazine, RE: PORTER. It is a stylish guide to the hottest restaurants, boutiques, and events currently making the hipster lists in both Canada and the states. It would be a fun, informative read if you forgot to download your favorite podcast before takeoff.

Most flights to the city arrive at Pearson International Airport (YYZ), a 30-45-minute drive from downtown, depending on traffic. Conveniently, though, Porter Airlines flies into Billy Bishop Airport (YTZ), also known as Toronto City Center Airport, located less than 15 minutes from downtown. There is one caveat: Billy Bishop is located on an island, and fairy access to the mainland departs every 15 minutes. Not at all inconvenient but just something of which to be aware.

Toronto, only slightly larger geographically than Chicago, isn’t huge. Still, I’d recommend renting a car as opposed to relying solely on Lyft and Uber. This is because parking is plentiful. For example, each day of our visit we stopped at the Art Gallery of Ontario (more on that later), and each day we parked directly in front of the museum during even its busiest hours. The longest we were forced to walk anywhere from our car was a block, maybe a block and a half. Am I talking too much about parking? Agreed. Let’s move on.

Where to stay in Toronto

The Anndore House Hotel in Toronto

Hold On, We’re Going Home: The Anndore House Hotel

The Anndore House

The Anndore House is my home for the next few days. Only a week old, this 4-star boutique hotel was a sad Comfort Inn a short time ago. Now it’s a meticulously designed chic oasis, already rated as Superb by the discerning travelers on TripAdvisor. It is new — very new — and almost all new hotels are beautiful. Still, I expect the details here to wear well over time. Anyone currently redesigning their bathroom has at least considered a look identical to the one here: white subway tile, gold brass fixtures, iron black framing. It’s a hot look, and it feels clean. In fact, clean describes well not just the bathroom design but also the dressing and living areas. Carpets, which in public spaces give me the heebie-jeebies, are replaced with concrete floors and low-pile area rugs. The usual coffee machine is instead a bright red SMEG kettle, accompanied by an assortment of tea and instant coffee. Black walls make the room appear spacious, larger than it is. A rotary-style phone and vinyl record player provide just a dash of kitsch. I will definitely start my hotel search with The Anndore when staying in Toronto again.

Below the guestrooms, the hotel offers a posh restaurant, bar, and barbershop. Unfortunately for me, room service is not available for another four days. So, I took my lazy bones downstairs for a quick bite.

Constantine at The Anndore House Hotel
Constantine at The Anndore House Hotel

Constantine at The Anndore House Hotel

Constantine at The Anndore House Hotel


If a hotel is almost always aided by its newness, restaurants are almost always hindered by it. There’s no time to soak in feedback, learn from clientele what works, toss what doesn’t. The menu can sometimes be unfocused. Of course, after a few months, a rhythm hopefully develops, and dependably great food finds its way to the patrons who faithfully stuck around. To be clear, Constantine isn’t bad by any means. It’s just forgettable. I had the Kale, Rutabaga, and Feta salad followed by their Lamb Pizza. The salad was colorful, interesting, and the unexpected mix of spice and sweetness harmonized wonderfully together. It was the flatbread pizza that dropped the baton. With no dominant flavor to latch onto, I found the mixture of meat and muddle boring.

Hotel restaurants vary wildly from inspired to insipid, and at least it’s trying. I expect, with time, it will only get better.

5AM in Toronto: The Art Gallery of Ontario

The Art Gallery of OntarioThe Art Gallery of Ontario

The Art Gallery of Ontario

The Art Gallery of Ontario in Toronto

The Art Gallery of Ontario

Let’s discuss my own failures. The Art Gallery of Ontario (AGO) is currently hosting Yayoi Kusama’s Infinity Mirrors, and advance tickets are sold out, but a small number of tickets are offered daily starting at 10 a.m. Art lovers begin securing their spot around 6 a.m. Each day I grabbed a coffee, hopped in line, and waited. Two hours was the most I could do before my conscious called into question my priorities, which is why each day I failed.

Fortunately, there’s much worth seeing in AGO even without a ticket to Kusama’s exhibit. The European Collection is a personal favorite, with works dating back to the second century. It includes Rembrandt, Monet, and Van Gogh, to name a few.

Energy: A Visit to Kensington Market

Kensington Market

A man dressed as Spiderman stays perches himself atop a fire hydrant while a reggae version of some top 40 hit blasts in front of a restaurant serving jerk chicken pasta. Kensington Market is the concentrated nucleus of Toronto’s multiculturalism. It is colorful, vibrant, and authentically bohemian. This food here is fantastic, and long lines are seen snaking out of a few famous dives. Try Rasta Pasta for the Italian Caribbean cuisine you never knew you needed.

Best I Ever Had: Brunch at The Drake Hotel

The Drake Hotel in Toronto

Brunch at the Drake Hotel in Toronto

Brunch at the Drake Hotel in Toronto

Rooftop of the Drake Hotel in Toronto

The Drake Hotel

Visiting a hotel called Drake for brunch while in Toronto is me at peak basicness. No, its name isn’t taken from you-know-who nor the legendary Chicago hotel. The Drake Hotel in Toronto is its own thing, a hodge-podge of millennial catnip: an airy rooftop bar, upscale boho dining scene, music venue, and art gallery all-in-one.

Weekend brunch is served here and at The Drake Commissary, the hotel’s outlier bar and everything from scratch bakery. This is an excellent example of a hotel restaurant done right with a well-curated menu and standout signature items.

Hubby and I ordered the Chicken and Waffles, a Drake Benny with salmon and mushrooms, Drake fries with pecorino and truffle butter, and a side of Naked Greens because healthy. The fries are crisp on the outside and soft and buttery inside. This variation of Eggs Benedict is made with a healthy portion of well-prepared and nicely plated salmon under a flavorful dollop of hollandaise sauce. The oven-roasted mushrooms, while delicious, added little to the overall dish. I’d recommend skipping this $3 addon. While we seem obsessed with Chicken and Waffles stateside, I saw no one order the brunch staple but me, and it was one of the best C and W’s I’ve ever had in life. Strawberries, hand-whipped cream, and (of course!) maple syrup played well with well-seasoned chicken fried to perfection. The naked greens were a refreshing palette cleanser.

Cocktails tend to be weak in Canada, but you can’t go wrong with a mimosa.

Sorelle and Co in Toronto
Sorelle and Co.

Shopping in Yorkville
Shopping in Yorkville

Most Instagrammable Places in Toronto

Sorelle and Co

Dineen Outpost

Rush Lane (for street art)

Yorkville (designer shopping neighborhood)

Vog Vault inside of John Fluevog Shoes on Queen Street.

Toronto Island

La Cubana brunch in Toronto
La Cubana

Tiene tumbao?

Try La Cubana. The location on “Roncy” serves an amazing Sunday brunch!

If you forget your Clinique facewash and your Smashbox lipstick, but you also want a beer.

Try Shoppers Drug Mart. It’s the most helpful place on earth, and it’s everywhere.