9 Best Bars in Harbourfront, the Entertainment District, and The Financial District, Toronto

Hidden in plain sight on the upper level of the Waterworks Food Hall, a former pipe and plumbing factory, this decadent art nouveau cocktail bar captures Toronto's \"Roaring '20s\" with its deliberate tribute to the building it's housed in. The menu features ingeniously crafted libations with cheeky industrial names like a Pounding Sand or the Strickling Bar. No ingredient goes to waste on the palate here, but the real catch is the bar's \"water program\" that features demineralized Toronto tap water that's been remineralized to replicate the profiles of popular springs from around the world. Tasty fusion snacks from the food hall below can also be ordered.

Since it was founded in 1973, Toronto's Second City—the younger sibling of the Second City in Chicago—has been showcasing some of the best comedy in Canada. Regular features include sketch comedy, improv battles, and seasonal revues. The recently re-opened complex houses three theaters and a restaurant, The Bentwood, with pricing running from C$15 to C$50 depending on seating and the show. 

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.

The hotel'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.

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$10 and C$26. 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.

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.