8 Best Nightlife in Harbourfront, the Entertainment District, and The Financial District, Toronto

Though it's primarily a restaurant, Canoe, on the 54th floor of the Toronto-Dominion Bank tower, is worth a trip just for a drink at the bar and a panoramic view of the lake. It has what might be the city's best Niagara wine selection and an extensive list of international bottles, as well as cocktails and beer. It's popular with finance types from the neighboring towers, who suit the swank surroundings. Go just before sunset to make the most of the view.

This brewpub features two massive bars with more than 10 local brews on tap, an open-concept kitchen with an imported Italian wood-burning pizza oven, and a sprawling patio with stunning views of the Toronto Islands. The building, a former 1930s boathouse, also houses a brewery; tours and beer tastings are available daily. Tours are free, but book in advance.

Located in the heart of the Financial District, this culinary oasis is popular with the business suits that work in the area. Don't let that keep you away though, because this downtown hotspot offers a sun-filled patio that's hidden from the hustle and bustle of Wellington Street. Bartenders whip up phenomenal cocktails while the kitchen creates harmonious textures and flavors on your plate.

The Shangri-La's spacious Lobby Lounge is famed for its high tea service complete with decadent pastry selection. The vibe gets swish by night as it transforms with live music, trendy cocktails, and delicious bar bites.

If you want to "see and be seen" in the Financial District head to this vast restaurant and bar, which has a wraparound year-round patio facing both Front and Yonge Streets. The O&B has become the destination for Bay Street's movers and shakers. Check out the impressive cocktail menu.

No hole-in-the-wall sports bar, this sleek 25,000-square-foot space adjacent to the Scotiabank Arena lights up with almost 200 high-definition flat-screen TVs and amazing sightlines from every club-style booth, table, or stool at one of the three bars. Head to the second floor to watch a game on the biggest TV, an HDTV screen two stories high. For popular sporting events, or any day or night the Jays, Leafs, or Raptors play, it's best to make a reservation (accepted up to three weeks in advance), though the bar does keep a third of its seats for walk-in traffic an hour before face-off.

The Steam Whistle Brewery, located on historic railway premises, makes an authentically crafted pilsner. There's a tasting room with a full food menu, a Munich-styled biergärten, and special events like Oktoberfest and the biannual (winter and summer) Roundhouse Craft Beer Festival. It's a great place to stop before or after a Blue Jays game.

Part of a Canadian comedy franchise, this venue headlines stand-up comedians on the rise (Jim Carrey and Russell Peters performed here on their way up), with covers usually between C$11 and C$25. Admission is C$5 on Tuesday for amateur night. The small space is often packed; getting cozy with your neighbors and sitting within spitting distance of the comedians is part of the appeal. Booking a dinner-and-show package guarantees better seats.