Where to go for an epic night out in Toronto

Whether you’re celebrating a special occasion, heading out on a first date or just unwinding with friends, an amazing night out in Toronto is the perfect balm for the soul—and Bloor-Yorkville has everything you need for an unforgettable experience from start to finish.

2 p.m.: Prep with a glow-up

Majesty’s Pleasure (102 Yorkville Ave.) Prepare yourself for the night ahead by sipping a mojito and noshing on tiramisu caramels at this super-stylish social beauty club, where you can indulge in an extensive array of treatments, including manicures, pedicures and massages.

Not to miss: Craving an out-of-this-world experience for you and your friends? Round up four to eight of your besties and enjoy spa and salon services with drinks and bites in a semi-private space.

Radford Studio (Yorkville Village, 55 Avenue Rd.)

Founded by makeup artist and entrepreneur Victoria Radford, this studio specializes in personalized skincare and beauty treatments, from brow shaping and lash tinting to facials, wrinkle relaxers and professionally administered medical injectables. You’ll leave looking your best for an evening adventure.

Trending: Try a popular service like the hydrafacial, hollywood north facial or custom facial, or opt for an eye-makeup-only or full-face-and-eye-makeup application, featuring hydrating skincare and undereye patches for a flawless finish.

Salt Beauty and Co. (122 Cumberland St.)

Want to make a more dramatic impression or try something daring with your hair? Let Salt’s expert stylists and colourists work their magic to bring out your natural beauty through masterful haircuts, hair colour and hair extensions in a warm and welcoming environment.

Not to miss: Get a free hair gloss treatment with any colour service, available until the end of March.

4 p.m.: Find your evening ensemble

Holt Renfrew (Holt Renfrew Centre, 50 Bloor St. W.) Looking to turn heads in stylish attire? This is your premier one-stop destination for elevated clothes, footwear and accessories. Holt’s convenient flagship location in the heart of Bloor-Yorkville offers outstanding options from many of the world’s most coveted designers and brands.

What’s new: Explore exhibitions, pop-ups, panels and entertainment in Holt’s newest in-store space, ON 3. It’s an inviting intersection of self-expression, style, culture and community, highlighting men’s and women’s fashion, beauty and grooming.

Loro Piana (111 Bloor St. W.) Discover elegant, expertly crafted cashmere and vicuña-wool ready-to-wear pieces from this Italian luxury brand. This flagship Canadian location is a must-visit shopping destination for men’s and women’s knitwear, footwear, fragrance and accessories.

What’s new: The Maison’s Spring/Summer 2025 collection marks a new chapter in its 100-year history, with dynamic, naturally flowing pieces inspired by the textures and shapes of Casa das Canoas in Rio de Janeiro.

7 p.m.: Dive into dinner

Buca Osteria and Bar (53 Scollard St.) Seafood aficionados will relish Buca’s wide selection of sumptuous dishes, including dry-cured swordfish, octopus carpaccio and seared New England scallops, which are often as unique in flavour as they are beautiful in presentation.

Not to miss: Enjoy popular menu items, including polpo e vongole, braised B.C. octopus, clams, bone marrow, crisp artichoke, cavolo nero, fregola sarda, and the salumi di mare, cured and air-dried for 14 days, which showcases the essence of the sea in every bite.

Enigma Yorkville (23 St. Thomas St.) For discerning foodies or anyone looking for a unique experience in addition to globally inspired cuisine, chef Quinton Bennett’s imaginative eight-course blind-tasting menu is not to be missed. This Michelin star restaurant offers dynamic, seasonal dishes that seamlessly blend the finest local and international ingredients.

What’s new: Enigma’s newly renovated fine dining space boasts floor-to-ceiling windows, marble floors and copper pendant lights dripping from a mosaic-tile ceiling. Expect a fresh, European-inspired experience showcasing a dedication to creativity, precision and hospitality.

Trattoria Nervosa (75 Yorkville Ave.) Highly acclaimed Canadian restaurateur Janet Zuccarini brings elevated southern Italian pizza and pasta dishes to Bloor-Yorkville. Choose from such classics as rigatoni bolognese and Calabrese pizza, and tasty signature dishes like the luscious barolo-braised beef-short-rib-based risotto.

Not to miss: Stop by from 3 p.m. to 5 p.m. to take advantage of the newly launched happy hour menu, which offers classic cocktails like the negroni, Aperol spritz and espresso martini, a selection of wine and beer, plus fresh pizza and pasta.

Ladurée Yorkville (162 Cumberland St.) Indulge in an exceptional dessert from Ladurée’s charming tea salon. Savour an assortment of decadent cakes and French pastries as you sip a latte or cappuccino while enjoying the Parisian-inspired atmosphere.

Trending: Enjoy bestselling treats like the Marie-Antoinette macaron, filled with delicate notes of rose, black tea, citrus and honey, or the pistachio macaron, offering a slightly sweet, nutty taste complemented by rich pistachio buttercream.

9 p.m.: Converge over cocktails

D|bar (Four Seasons Hotel Toronto, 60 Yorkville Ave.) World-renowned chef Daniel Boulud’s lively cocktail bar serves up inventive drinks, including a chilli-pepper-infused spiced-pineapple margarita, as well as plenty of non-alcoholic options (“nulled wine,” anyone?). Shareable plates, like beef carpaccio, burrata and charcuterie, will satisfy the cravings of every foodie at your table.

Not to miss: Set the stage for a vibrant evening with live entertainment. Enjoy spotlight artists on Wednesdays from 6 p.m. to 9 p.m.; a pianist on Saturdays from 2 p.m. to 5 p.m.; and DJ sets from Bellosound on Thursdays from 8 p.m. to midnight and on Fridays and Saturdays from 9 p.m. to 2 a.m.

The Gatsby (Windsor Arms Hotel, 18 St. Thomas St.) Relaxed opulence is the best way to describe this restaurant and bar, where you can sip creative cocktails, browse its 500-label wine list and enjoy succulent dishes like charcoal-grilled prime beef striploin, milk-fed veal and fresh-herb-crusted rack of lamb.

Not to miss: Every Thursday and Friday, enjoy live music to stir the senses and soothe the soul.

Skylight Rooftop (W Toronto, 90 Bloor St. E.) As its name suggests, this enchanting and playful oasis delivers impressive views of Bloor Street and the city skyline. Mezze dishes and a Mediterranean-focused raw bar complement the signature cocktails curated by Skylight’s brilliant beverage manager, Olivia Arezes.

Not to miss: Elevate your experience with signature cocktails like the Clarified Pistachio Martini, Skylight Smash, Go Figure Old Fashioned and Wish You Roses Margarita, which perfectly complement the seasonal, coastal-inspired flavours in the dishes.

Writers Room Bar (Park Hyatt Toronto, 4 Avenue Rd.) An homage to its history as a gathering spot for Canadian authors, writers and creatives, this sophisticated rooftop bar features floor-to-ceiling windows, shareable plates and breathtaking views of the city. Skilled mixologists prepare novel, spirit-forward cocktails—some of which are even prepared tableside!

Not to miss: Enjoy chilled seafood alongside stirred cocktails inspired by iconic Canadian literature, like the Bitter Relief, a tribute to Margaret Atwood’s Cat’s Eye, and Bookends, paralleling Jack McClelland’s Imagining Canadian Literature: The Selected Letters of Jack McClelland.

Discover more options for an unforgettable night out in Bloor-Yorkville.