$$$$Cocktail barLittle ItalyDaily 13:00-01:00
Bar Raval on College runs vermouth on tap and Spanish bar snacks from a mahogany Art Nouveau counter since 2015, Grant van Gameren's room the Michelin Bib.
OrderA vermouth on the rocks with a slice of jamon iberico.
TipWalk-ins only. Arrive before 17:30 for an easy stool; the doors open at 13:00 every day of the week.
$$$$Cocktail barLittle ItalyMon-Thu 16:00-01:00, Fri-Sat 16:00-02:00
Bar Pompette on College Street is the aperitif bar above Pompette since 2018, North America's 50 Best Bars ranked #8 in 2026 with a low-ABV cocktail program.
OrderThe signature Pompette Spritz or whatever the bar is pouring on draft.
TipReservations through Tock. The downstairs Pompette is the restaurant; bar is upstairs.
$$$$Cocktail barThe AnnexDaily 17:00-02:00
Civil Liberties on Bloor at Ossington runs a no-menu speakeasy since 2014, bartenders mixing drinks to your taste in an industrial-vibe back room.
OrderTell the bartender three flavours you like and let them mix.
TipNo menu by design. The door at 878 has no signage; ring the bell. Late nights until 02:00.
$$$$Cocktail barQueen WestTue-Sun 18:00-02:00
BarChef on Queen West is Frankie Solarik's modernist cocktail bar since 2008, theatrical drinks with dry ice, smoked glass domes and botanical foams.
OrderThe signature smoked Manhattan presented under a glass dome.
TipReservations recommended; cocktails run $25 to $50. Closed Monday.
$$$$Cocktail barKensington MarketTue-Sun 18:00-02:00
Cocktail Bar on Dundas West is Jen Agg's drink room since 2013, the menu split seasonal, bold, citrusy, liquor forward and wild cards, sister to Grey Gardens.
OrderWhatever the bar manager David Greig is excited about that night.
TipClosed Mondays. Snacks from Grey Gardens kitchen run light. Bar seats walk in; tables on Resy.
$$$$Cocktail barOssingtonWed 18:00-00:00, Thu 18:00-01:00, Fri-Sat 18:00-02:00
Bar Mordecai on Dundas West is a retro Wes-Anderson cocktail room since 2020, World's 50 Best Discovery list with vintage and modern drinks.
OrderThe Mordecai Martini, served with house olives.
TipNo reservations; small room fills early on weekends. Closed Sunday-Tuesday.
$$$$Cocktail barKensington MarketTue-Sun 19:00-02:00
Mahjong Bar on Dundas West pours Asian-inspired cocktails behind a Vietnamese sandwich-shop facade since 2016, a speakeasy through the back door.
OrderA Pandan Highball with the bahn mi sliders.
TipEnter through the sandwich shop; the back door opens after 19:00. Reservations on Resy.
$$$$Cocktail barOssingtonTue-Sun 17:30-02:00
Pinkerton's Snack Bar on Gerrard East is the city's reference snack-and-cocktail dive since 2017, owner Marc Baglio's pan-Asian plates and drinks.
OrderA house cocktail with the bao buns and crispy rice.
TipWalk-ins only. Closed Monday. Late nights to 02:00 Friday and Saturday.
$$$$MexicanLittle ItalyMon-Tue 11:00-03:00, Wed-Thu 11:00-04:00, Fri 11:00-04:30, Sat 09:00-04:30, Sun 09:00-03:00
Sneaky Dee's at College and Bathurst runs the city's reference late-night Tex-Mex kitchen until 04:30 on Friday and Saturday nights since 1987.
OrderThe King's Crown Nachos with a pitcher of Stella.
TipCash only at the till; debit card at the bar. Late-night kitchen the city's most reliable after-bar option for nachos.
$$$$Cocktail barOssingtonDaily 16:00-02:00
The Communist's Daughter on Dundas at Ossington is the strip's reference dive bar since 2003, a former Portuguese diner with low ceilings and cheap beer.
OrderA pint of local lager with a shot of rye.
TipCash preferred under $10. Late kitchen has frozen pizzas after 22:00.
$$$$Cocktail barOssingtonWed-Sun 17:00-02:00
Miss Thing's on Queen West in Parkdale runs Polynesian tiki cocktails and Pacific Rim plates since 2013, the painted bamboo interior the strip's reference.
OrderA classic Mai Tai with the salt-and-pepper squid.
TipClosed Monday and Tuesday. Weekend nights take walk-ins after 22:00 only.
$$$$Cocktail barLittle ItalyWed-Thu 17:00-00:00, Fri-Sat 17:00-02:00, Sun 16:00-23:00
Track & Field on College Street is the lawn-games cocktail bar that returned in October 2021, two floors with bocce, shuffleboard and a photo booth.
OrderA round on the bocce court with a tapped cocktail.
TipWalk-ins or Tock reservations for the bocce lanes; 30ft bar runs through the main floor.