botanical-heightsMon-Sat 11:00-01:00, Sun 11:00-23:30
The Shaw outpost of Sasha's pours the same wide by-the-glass list and noshing plates near the Botanical Garden, a relaxed neighbourhood wine bar.
Signature pour: A by-the-glass pour to match the board
Wine focus: Approachable Old and New World by the glass
Food: Cheese, charcuterie and small plates
Tip: It works for a glass before dinner near the Botanical Garden. The board-and-glass pairing is the move here too.
webster-grovesThu-Sat 17:00-22:00 (cafe daily 07:00-14:00)
By day a neighborhood cafe, Thursday to Saturday The Clover and the Bee turns its candlelit room into a natural wine bar with producer-led bottles and snacks.
Signature pour: A natural rose or skin-contact pour
Wine focus: Natural producers, sourced person-by-person
Food: Italian-leaning snacks, sweets and small plates
Tip: Come Thursday through Saturday after 5pm for the natural wine list; the kitchen leans Italian and sweets travel well by the glass.
richmond-heightsMon-Sat 10:00-19:00, closed Sun
Parker's Table is a beloved boutique wine, beer and gourmet shop in Richmond Heights with a tasting bar, a go-to for staff-guided bottle picks and provisions.
Signature pour: A staff-recommended boutique bottle
Wine focus: Boutique wine retail with tasting bar
Food: Cheese, charcuterie and gourmet provisions
Tip: Tell the staff your budget and the meal; they are excellent at matching a bottle. Strong cheese counter too.
central-west-endMon-Sun 16:00-24:00
Kevin Brennan's Central West End bar pours a deep wine list with small plates across a townhouse of rooms, from a fireside lounge to a basement bar and patio.
Signature pour: A by-the-glass pour from the deep list
Wine focus: Deep global list with by-the-glass range
Food: Small plates, cheese and cigars
Tip: The multi-room layout suits any mood; ask the bar for a by-the-glass recommendation. Cigars are sold for the patio.
midtownMon-Sun, lunch through evening, later on show nights
At City Foundry in Midtown, City Winery pairs house-made and curated wines with a full restaurant and a live-music room, a wine bar built around the stage.
Signature pour: A glass of City Winery's own production
Wine focus: House-made and curated eco-friendly wines
Food: Full restaurant menu
Tip: Pair dinner and wine with a concert; check the calendar. The on-site production wines are worth a flight.
maplewoodWed-Sun, afternoon through late, closed Mon-Tue
Side Project's Maplewood Cellar is a Belgian-inspired beer bar that also pours a deep whiskey and wine list, the tasting room for the metro's top brewery.
Signature pour: A pour from the Side Project lineup
Wine focus: Belgian-inspired beer plus whiskey and wine
Food: Snacks and light bites
Tip: It is beer-forward but the wine and whiskey lists are serious too. A short walk from the brewery itself.