Bar Hop Itinerary: Your Bloor-Yorkville Guide

Planning a night out has never been easier. Bloor-Yorkville is home to some of the best bars, wine bars, and pubs in the city, from casual rooftops to intimate wine bars, or more extravagant spaces, there’s a go-to option for every preference. If a memorable experience is what you’re looking for, a Bloor-Yorkville bar hop should top your list of social outings. Plus, once the warmer nights hit, you can find the best patios in Toronto here.

Best Bars in Bloor-Yorkville for Your Upcoming Bar Hop


Sofia restaurant and bar features contemporary art and weekday happy hour

JLo on your mind? If you want to lounge where the queen of TIFF 2019 celebrated, Sofia can make your dreams come true. The interior design is a reason to visit on its own, featuring artwork from Banksy, Basquiat, Dine, Mr. Brainwash and Andy Warhol. Located next to Tagliatella Galleries, the artwork found on the walls of Sofia are constantly refreshed with pieces available next door at the gallery.

Aside from the aesthetic experience and the lingering glamour of JLo, Sofia offers Happy Hour Monday-Friday! From 5 pm – 8 pm you can enjoy half-price cocktails and select wine, at both the bar and courtyard patio.

99 Yorkville Avenue

Bar Reyna

Bar Reyna is an escape to the Mediterranean, without having to make any travel plans. Set in a two-storey classic Victorian townhouse with a back patio that feels more like a treehouse, Bar Reyna offers a relaxed atmosphere and great gathering space. Their extensive cocktail list is filled with creativity with ingredients you’ve likely never considered! Happy Hour is offered from 3-6pm daily and features a selection of $7 snacks and drinks, including their Kiwi Chili Margarita!

158 Cumberland Street

Earls Yorkville

With a dedicated Happy Hour menu and a kitchen and bar open until 1am from Sunday to Thursday, consider Earls Yorkville to kick off or finish your night out. Their Happy Hour menu does not disappoint, with everything from $4 tacos to $10 cocktails. Mixed with vegetarian options, seafood, and shareable items like pizza or seafood platters, Earls is a great gathering space for groups or celebrations. While great for late nights from Thurs-Sun, Earls Yorkville also has happy hour from 2pm – 5pm every day of the week.

55 Bloor Street West, Manulife Centre

Skylight at the W Hotel

Skylight is an enchanting rooftop located on the 9th floor of the W Hotel, featuring bohemian decor and cozy couches, making the perfect backdrop for a fun night out.

Overlooking Bloor Street, you can catch the sunset as you enjoy the shared plates and cocktail menu! The space is an indoor-outdoor oasis creating an escape from the city in a fabulous setting.

9th Floor, 90 Bloor Street East

The Oxley Public House

Dark green interior of The Oxley bar featuring brown leather bar chairs

Set in a gorgeous Yorkville Avenue townhouse, The Oxley is an inviting environment reminiscent of a welcoming British home. With plenty of space inside, as well as two patios and a bar area, you can choose between more secluded environments or those overlooking the streets of Bloor-Yorkville.

Priding themselves on an extensive beer and wine list, The Oxley also offers a well-curated list of house cocktails and, of course, traditional British dishes.

121 Yorkville Avenue


Tucked along a quintessential Bloor-Yorkville alleyway is the somewhat fabled Alobar Yorkville. One of three “Alo-sister,” restaurants, Alobar offers a variety of ways to unwind: the lounge area, open dining room, traditional bar for walk-ins, or the outside terrace seating, which is surrounded by lush greenery and overhead fairytale lights.

Not only does Alobar offer curated wine lists and cocktails, but also an exquisite menu created by renowned chef, Patrick Kriss. Plates are designed to share and also include a variety of desserts. Alobar was recently awarded 1 Michelin Star.

Thursday to Saturday Alobar offers extended cocktail and wine hours from 4:30 pm – midnight.

57a 162 Cumberland Street

The Pilot

The expterior view of The Pilot which offers three floors and a rooftop
The Pilot

An institution in itself, The Pilot has been a Bloor-Yorkville staple for over  75 years! It’s a multi-level venue with a genuinely relaxed atmosphere, creating a welcome escape from the outside world. The rooftop, otherwise known as The Flight Deck, is open March to December and features a full food and drink menu. With space for 185 people, The Flight Deck is perfect for larger groups

There’s also the main-floor bar which hosts live jazz every Saturday from 2:30 pm – 5:30 pm. This space has a lot of history and a friendly atmosphere, making it a repeat choice among locals.

22 Cumberland St

Writers Room Bar, Park Hyatt Toronto

Writers Room Bar

This one is for cocktail lovers! The recently redesigned Park Hyatt Toronto is exquisite in both its design and the quality of its food and drink. The Writers Room Bar, located on the 17th floor, features stunning views of the city skyline and a gorgeous rooftop for the warmer months. With an emphasis on “reimagined classics,” the cocktails are a modern interpretation while featuring classic and approachable flavor profiles.

Designed to pair effortlessly with the food menu, guests can browse a selection of shared plates and desserts.

4 Avenue Road

d|bar at the Four Seasons

The velvet couches and plush oversized lounge chairs make d|bar at the Four Seasons immediately feel like home (a very well-decorated home). The comfort level makes d|bar a great end-of-evening stop, but the cheese boards and charcuterie also make the case for a great starting point.

Led by Melissa Hart, the cocktails at d|bar are a fusion of her culinary background and passion for mixology. The ingredients in the craft cocktails are focused on seasonal, high-quality offerings.

For anyone wanting to fend off the Sunday Scaries, stop by on Sundays from 9 pm-close for a live DJ night.

60 Yorkville Avenue

Hemingway’s Restaurant & Bar

Hemingway's features 3 patios

Another Bloor-Yorkville classic, Hemingway’s has been at home in Bloor-Yorkville for over 40 years! The space features three bars, restaurant seating, and four patios (including heated, covered patios during the winter), along with daily specials and 24 draught beers on tap!

Complete with screens for game nights and a variety of weekly events, Hemingways is a gateway to community engagement. Events include Silent Disco Night, Themed Trivia, Live Music, and both local and international sports nights. Whatever night of the week you choose, it’s certainly a must-visit for a well-executed bar hop.

142 Cumberland Street