Kandice VincentToronto’s Annex neighborhood is one of those places that just oozes character. Known for its Victorian homes, indie bookstores, artsy cafes, and bustling student energy (thanks to nearby U of T), it’s where you can spend the whole day wandering.
But when the sun goes down, the Annex really comes alive with its amazing bar scene.
I just love hopping from bar to bar with my friends, sipping creative cocktails, and grabbing late-night bites. And these bars are all Insta-worthy, too—some with cozy, candlelit vibes and neon-lit patios with music.
If you’re ready to plan your next unforgettable night out, here’s my curated guide to the coolest Annex bars in the city. Enjoy!
C Suite
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OpenTable: https://www.opentable.ca/r/c-suite-toronto
Instagram: https://www.instagram.com/barcsuite
Address: 126A Cumberland St
Hours: Tue – Wed, Sun: 5 PM – 12 AM
Thursday: 5 PM – 1 AM
Fri – Sat: 5 PM – 2 AM
Contact: (416) 386-4611
Must-Order: Cafe Cumberland
Have you ever sipped cocktails in a 1920s train car? Well, now’s your chance! C Suite in Yorkville offers plush lounge seating and a sleek bar setup that makes you feel like you’ve stepped back in time.
If you sit at the bar, the barman will craft unforgettable drinks tailored to your taste. Each cocktail starts at $40—a bit of a splurge—but trust me, it’s worth every dollar.
One drink you have to try is Cafe Cumberland. It’s what an espresso martini wants to be when it grows up—strong, velvety, and perfectly balanced.
Note that the place limits groups to a maximum of four people, with bar seating starting at 6 PM and lasting about three hours. The lounge area is also beautiful if you prefer a more relaxed vibe away from the action.
Pro Tip:
While you’ll be served complimentary champagne and truffle potato chips from France, we recommend grabbing dinner first before heading to C Suite. Their food menu is very limited, so come full and ready to sip the night away.
The Annex Hotel Lobby & Cafe
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Website: https://theannex.com/
Instagram: https://www.instagram.com/annexhotels/
Address: 296 Brunswick Ave
Hours: Mon – Sun: 8 AM – 11 PM
Contact: (647) 694-9868
Must-Order: Annex Martini
The Annex Hotel Lobby & Cafe is a place that effortlessly transforms from a bright, artsy cafe in the morning to a stylish bar by evening. Designed by a Montreal-based studio, this space is filled with stunning artwork and lovely furnishings.
Their bar menu is simple but impressive, focusing on quality over quantity. Drinks are crafted with care, and the bartenders are always down to recommend something new based on your taste.
My personal go-to is the Annex martini, a refreshing mix of London Dry Gin, St Germain, and lemon. It’s crisp, bright, and dangerously easy to sip on.
If you want something to nibble, their kitchen serves up light, shareable snacks like delicious cured meat and cheese plates. These pair perfectly with their extensive selection of rare, biodynamic, and organic wines from around the world.
Pro Tip:
Planning a special event? The Annex actually allows you to bring your own cake, and you can request other accommodations to make your celebration extra fun and memorable.
Crafty Coyote
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Website: https://craftycoyote.ca/
Instagram: https://www.instagram.com/craftycoyoteto
Address: 511 Bloor St W
Hours: Mon – Sun: 11 AM – 2 AM
Contact: (647) 748-2338
Must-Order: Crafty Coyote Amber Lager
Crafty Coyote is one of those Annex pubs that instantly feels like home. With a strong focus on craft beer (very homey), this bar is the perfect place to kick back with friends.
I love its interior because it has so much character. Imagine tables made from barrels and salvaged materials crafted by one of the owners, Sean, who also runs his own small furniture business.
What’s cool is that each dish comes with a suggested local beer pairing, featuring breweries like Sawdust City. You can also order a beer flight to try a little bit of everything.
If you’re not sure what to sample, go for their Crafty Coyote Amber Lager. It’s smooth, slightly malty, and just the right hint of caramel sweetness without being heavy.
Pro Tip:
Keep in mind that Crafty Coyote takes group reservations and private parties. Just reach out, and they’ll handle the rest, so you can focus on the fun.
Paradise Grapevine
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Website: https://paradisegrapevine.com/
Instagram: https://www.instagram.com/paradisegrapevine
Address: 841 Bloor St W
Hours: Mon – Sun: 1 PM – 2 AM
Contact: (416) 536-7178
Must-Order: X Bulles
Paradise Grapevine is a wine and beer bar known for its lush back patio. Open until 2 AM, it’s the perfect hangout spot for long summer nights with friends.
Their wine list is seriously impressive, featuring an extensive rotating selection of lower-intervention wines. These come from smaller producers and have a unique identity and flavor you don’t get from big labels.
We also like that they know how to serve wine properly. Some bottles are even opened a day early to let the flavors fully develop!
If you’re looking for a recommendation, my favorite is their sparkling rose X Bulles. It’s a juicy yet dry blend of Chardonnay and Grolleau, with tiny fizzing bubbles that give it an amazing mouthfeel.
Pro Tip:
Don’t miss Paradise Grapevine’s wine and cheese tastings every Thursday at 7 PM in their winery space. Expect to taste fresh new releases and special vintages, all paired with top-tier cheeses from their friends at Good Cheese.
Insomnia Restaurant and Lounge
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Website: https://www.insomniarestaurant.com/
Instagram: https://www.instagram.com/insomniatoronto
Address: 563 Bloor St W
Hours: Wed – Sun: 10 AM – 2 AM
Contact: (416) 588-3907
Must-Order: Diva
Known citywide for its late-night eats, Insomnia Restaurant and Lounge has been voted Best Late-Night Restaurant by Now Magazine. Yep, their kitchen is open until 2 AM.
But we’re actually here to focus more on another thing they’re famous for—their extensive selection of martinis. They’ve hosted Martini Madness for over 25 years, serving $8 martinis from 10 AM to 2 AM.
With 50 different martinis on the menu, it’s hard to choose just one. But my personal favorite is the Diva—a deliciously balanced mix of vodka, Alizé Red, grapefruit, cranberry, and sparkling wine.
Brunch lovers would love their boozy brunches. No surprise there since they’ve also been named by Now as Toronto’s Best Brunch Spot.
Pro Tip:
If wine is more your jam, check out Insomnia’s Wine Hour daily from 3 PM to 5 PM. It’s the ideal way to unwind with quality wines at brilliant prices.
Duke of York
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Website: https://dukepubs.ca/duke-of-york/
Instagram: https://www.instagram.com/duke_pubs/
Address: 39 Prince Arthur Ave
Hours: Mon, Sun: 12 PM – 10 PM
Tue – Thurs: 12 PM – 11 PM
Fri – Sat: 12 PM – 12 AM
Contact: (416) 964-2441
Must-Order: Spicy Mango Jalapeno Margarita
The Duke of York has been keeping locals happy (and buzzed!) for over 40 years. This British-style pub is great for students grabbing after-class pints or friends catching up over nachos, wings, and cocktails.
As you can imagine, their menu is packed with pub fare. In addition to loaded nachos and crispy wings, they offer hearty burgers, ribs, fish and chips, and lots more.
If you’re looking for a great deal, check out their Power Hours—between 4 PM and 6 PM, you can grab one of their season-inspired cocktails for just $10. My personal favorite is their Spicy Mango Jalapeno Margarita—fruity, fiery, and very addictive.
Before or after hitting the bar, you could swing by nearby attractions like ROM, Varsity Stadium, and Yorkville.
Pro Tip:
Don’t forget to drop by the Duke on Thursdays for their Burger and a Beer special. Starting at 4 PM, you can get a pint of Mill Street Organic Lager and their Junior Banquet Burger with fries for just $23.99!
Madison Avenue Pub
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Website: https://madisonavenuepub.com/
Instagram: https://www.instagram.com/madisonavenuepub/
Address: 14 Madison Ave
Hours: Mon – Sat: 11 AM – 2 AM
Sunday: 11 AM – 12 AM
Contact: (416) 927-1722
Must-Order: Stella Artois
The Madison Avenue Pub, or simply The Madison, is an Annex institution. Known citywide for its party-hard vibe and packed uni crowd, it’s the go-to spot if you want a wild night.
This mega-pub is seriously huge, with multiple floors, hidden sections, and spacious patios. There’s even a basement piano bar, as well as TVs, beer memorabilia, billiards tables, and dart boards.
When it comes to drinks, they have 20 different beers across 120 beer taps, which is very impressive. Prices are surprisingly solid, with a pint of Stella Artois at $9.95 or a pitcher for $28.09 (my favorite).
As for weekday deals, Thursdays are a favorite with $5 Amsterdam on tap, $5 rail drinks, and no cover. Mondays are pretty sweet, too, with half-priced wings and a free half-pint of Amsterdam for the first 50 guests.
Pro Tip:
The Madison enforces a dress code policy. Urban wear like tank tops, durags, and baggy or track pants is not allowed.
