Special Occasion Spots for a Night Out in Toronto this Holiday

Find Hotels

Whether you’re celebrating the holidays or just looking for cool restaurants to gather for an evening with friends or loved ones, Toronto has special occasion spots with that certain kind of sparkle. Local blogger and photographer, Krystle Ng-A-Mann, dishes on where to go out for any kind of celebration at this time of year.

Make the most of these longer nights this season with your favourite people. From Instagrammable interiors to one-of-a-kind dishes and experiences, to the most talked about hot spots around Toronto, these are the best for a night out with your nearest and dearest.

The piano bar at Sofia Yorkville: One of Toronto's stunning special occasion spots for a night out.
Sofia Yorkville

Sofia Yorkville

The newest hot spot in Yorkville and latest addition to the INK Entertainment empire in Toronto, Sofia Restaurant & Bar offers dining, entertainment, and art in one location. You can “eat your art out” on a selection of fine Italian dishes, while marveling at the opulent interior filled with red velvet chairs, Murano glass chandeliers, and Andy Warhol pieces on the walls.

Lunch is served daily and brunch is offered on Sundays from 11 a.m. to 3 p.m. But dinner is a special experience, with live music playing on most evenings. Lastly, if you’re in the mood for more art gazing, drop by the first Canadian location of Taglialatella Galleries next door.

The bar at Hotel X Toronto.
Hotel X Toronto

Hotel X Toronto

Hotel X Toronto is not just a hotel, but rather a luxury resort and entertainment complex. Summer nights can be enjoyed on its tri-level rooftop. But don’t let the cooler temps prevent you from visiting in the winter when you can still enjoy panoramic views of Lake Ontario and the Toronto skyline at Falcon SkyBar (open 365 days a year). There are 6 more distinct dining areas at the hotel, including the stunning Lobby Bar & Lounge.

The dining room of Constantine Restaurant Toronto.
Constantine

Constantine

On the ground level of newly opened The Anndore House on Charles Street, Constantine serves up fine dining ‘Middle-terranean’ (Middle Eastern and Mediterranean) with influences of coastal Italy in its well-appointed, 145-seat dining room.

Smoked Sea Bream Pâté, 30-day Dry Aged Rib Eye Steak, and Wagyu Picanha are just a few things on the dinner menu, which was created by Executive Chef Craig Harding (of Campagnolo restaurant). Is your mouth watering yet?

The dining room of Oretta Restaurant Toronto.
Oretta

Oretta

If you live in Toronto and spend any time on Instagram, chances are, you’ve seen a photo of the famous pink, white, and gold feature wall. is known to have one of the prettiest interiors in all of Toronto. On bustling King Street West, it has a prime location, and you can find a good selection of authentic Italian cuisine on the menu. You can reserve in the main dining room and the upstairs is great for private dining and large groups.

The bar at Chubby's Jamaican Toronto.
Chubby's Jamaican

Chubby’s Jamaican

Chubby’s Jamaican Kitchen combines awesome food, décor, and friendly staff, which is why it’s no wonder you’ll be greeted with a full house on most evenings here. You might recognize Chubby’s from its adorable pink upstairs bar that is plastered all over Instagram.

The menu is Jamaican-fusion and the cocktails have fun Jamaican-inspired names, like “Everything Nice” and “Gin and Ting”. My personal faves are the Saltfish Fritters, Pepper Shrimp, Oxtail Stew, “My Blossom” cocktail and “Calabash Bay”, which is served in a pineapple!

The dining room at Don Alfonso 1890 Restaurant in Toronto.
Don Alfonso 1890

Don Alfonso 1890

Don Alfonso 1890 is an upscale Italian restaurant that opened to much fanfare this past summer. It’s the first North American location of the Michelin-starred Don Alfonso of Italy and newest venture from The Liberty Group.

Chefs Alfonso and Ernesto Iaccarino serve elegant dishes like Ice Creamed Eel topped with sturgeon caviar, and Slow Cooked Egg Yolk surrounded by Burrata Foam. Choose from either a Classic or Contemporary Tasting Menu (both $150) in the main dining room or order à la carte in the Mezzanine Lounge.

The bar and skyline view at Bisha Hotel/KÖST bar in Toronto.
Bisha Hotel/KÖST

Bisha Hotel/KÖST

The Bisha Hotel is one of Toronto’s chicest spots. You can lounge at the Lobby Lounge of this swanky boutique hotel, or catch some of the nicest views of the CN Tower and Toronto skyline at KÖST, its restaurant on the 44th floor and one of the top hotel rooftop bars in the city.

The bar at Bacchanal Toronto.
Bacchanal

Bacchanal

Bacchanal means “an occasion of wild and drunken revelry”. While you won’t find any of that at Bacchanal, you will find an upscale French bistro food and cocktail menu offered in a beautiful space with blue, mustard and gold accents. Order à la carte or “Carte Blanche” ($85, $150 with wine pairings).

Diners at La Palma Restaurant Toronto.
La Palma

La Palma

100-layer Lasagna? Yes, it’s a thing, and one of the dishes La Palma is best known for! This all-day dining Dundas Street West restaurant (also a Chef Craig Harding & Alexandra Hutchison venture) has been a hit since it opened in 2017. The space is Venice Beach meets Toronto, and the dishes and cocktails are yummy (my faves are the Baked Eggs All’ Amatriciana and the signature “La Palma” cocktail).

The bar at Café Cancan Toronto.
Café Cancan

Café Cancan

If you haven’t seen photos of this cute French bistro all over Instagram, then you might be living under a rock. With interior design by Tiffany Pratt and food by chef/owner Victor Barry, Café Cancan has the best of both worlds.

Although it’s open for breakfast and lunch, there are unique offerings that can only be had at dinnertime. There is a wide selection of cocktails, wine, beer and even rosé on tap. With only 30 seats, you’ll definitely get warm and cozy in this intimate restaurant.

The bar at Ricarda's Toronto.
Ricarda's

Ricarda’s

Ricarda’s is an all-day restaurant – open for breakfast, brunch, lunch and dinner 7 days a week. Occupying the ground floor of the QRC West Building at 134 Peter Street, it has a spacious and beautiful 170-seat dining room, as well as an open-concept kitchen, “grab and go” counter, lounge and bar. The mainly Mediterranean menu is always evolving, so you’ll want to check back often.

The bar at The Broadview Hotel Toronto.
The Broadview Hotel

The Broadview Hotel/The Civic

The Broadview Hotel opened its doors in the summer of 2017 (taking over from the strip club, Jilly’s, that used to occupy the space) and has been a huge hit ever since.

On the ground level, there is a light and airy café, but the main attraction is the rooftop, which is one of the city’s most popular bars with a view. Its ground level restaurant, The Civic, opened early in 2018 and offers a contemporary take on a late 19th-/early 20th-century bistro menu.

The bar at The Commoner Toronto.
The Commoner

The Commoner

The Commoner is a newly opened ‘elevated pub’ in Roncesvalles Village. Featuring a spacious dining room and bar accented by oxblood banquettes, mustard bar stools, green wood panels and white subway tiled walls, and largely comfort food-based pub menu, it’s perfect as a special occasion spot in the winter. The 30-day dry aged New York Steak still has my mouth watering!

Food and a drink at Bar Raval Toronto.
Bar Raval

Bar Raval

Always a fave, Bar Raval is one of several bars and restaurants in the Grant van Gameren empire in Toronto (which includes Bar Isabel, El Rey, Harry’s, Pretty Ugly, Tennessee Tavern, and Rosalinda).

This intimate bar is one of the most popular places to grab a drink and authentic Spanish tapas in the city. Not to mention the Gaudi-style interior makes you feel like you’re smack dab in the middle of Barcelona.

La Banane

With a dessert on the menu called the “Ziggy Stardust Disco Egg”, you know you’re in for a totally eccentric experience at La Banane. But the individually splatter-painted, Easter egg-looking desserts created by chef Brandon Olsen are not the only reason you should go.

There are many other delicious and over-the-top menu items at this French restaurant on Ossington, like the Eurobass-en-croûte. La Banane also has a raw bar filled with sustainable and ethically-sourced fish.

About the Author

Krystle Ng-A-Mann is a local lifestyle Blogger with a passion for food, fashion and travel. Follow her adventures at Dine & Fash.