Toronto’s Best Holiday Date Spots

Are you looking for the best palce to take that special someone these holidays? Maybe finding the right place to set the vibes on the first date? Whether it’s the first date or the fiftieth (Adam Sandler, 50 First Dates, great movie), we’ve got you covered!

Experience the Holiday Magic at Bloor-Yorkville

Kick-off the holiday season in Yorkville with Holiday Magic 2022! Hosted by Traci Melchor of Canada’s Drag Race, the tree lighting ceremony will feature a performance by Chantal Kreviazuk and an appearance by Jeremie Albino! After their opening ceremony, you and your date can look forward to shopping, dining and taking in the neighborhood’s art and cultural attractions surrounded by the holiday lighting along tree-lined streets!

Where: Village of Yorkville Park, 115 Cumberland St, Toronto, ON, M5S 2W7.

When: Saturday, November 26th from 5:00 p.m. to Saturday, December 31st.

Price: it’s free!

Visit their website for more information!

Light Up the Tree at the Distillery District, Stay For Their Winter Village

Toronto’s most charming holiday market is back and is kicking off with the Winter Village Tree Lighting Ceremony! Make your way to the Distillery District for live entertainment, and the tree lighting ceremony will begin at 6:00 p.m., then come back for the 65+ local merchants, restaurants, and cafés, plus additional seasonal vendors and food cabins

Where: 55 Mill St, Toronto, ON, M5A 3C4.

When: Thursday, November 17th at 5:00 p.m. to Saturday, December 31st!

Price: $-$$.

Visit their website for more information!

Grab a Drink at The Thirsty Elf at the Fairmont Royal York

The Thirsty Elf is one of the more sophisticated celebration spots this holiday season, held inside the Fairmont Royal York! With Christmas sweaters, kitschy décor and cheerful, and festive cocktails, the Thirsty Elf has everything you need to get into the spirit of Christmas! Get ready to Gin-gle all the Way, and this time, it’s okay if you find yourself on the Naughty List; it’s made with cranberry, cinnamon, lime, ginger beer, Northern Keep Vodka, and mint!

Where: 100 Front St W, Toronto, ON, M5J 1E3.

When: Open Thursday through Saturday from Thursday, November 17th to Saturday, December 17th.

Price: $$.

Visit their website for more information!

Skate and Dance at the Union Holiday Public Skating Rink

Part of Union Holiday, there will be a free outdoor skating rink at Union Station! Enjoy one of Canada’s favourite activities in a scenic setting in the middle of downtown Toronto, and if you get the chance, do it on one of the Union Beats Skate Nights, where local DJ’s will be mixing live from rinkside to amplify your skating experience! Show off your skills, or take a dive and make your date look like a pro!

Where: 65 Front St W, Toronto, ON, M5J 1E3.

When: Tuesday, November 29th to Monday, January 2nd.

Price: it’s free!

Visit their website for more information!

Grab a Tube for Two at Mount Chinguacousy

Photo credit: Herman Custudio.

Is there anything more romantic than sliding down a hill at breakneck speeds with little to no control over your vehicle? Well, in most cases, there are probably a few things more romantic than that, but not at Mount Chingacousy! Snow tubing is so much fun, and this winter wonderland is one of the best places for it; plus, you don’t have to drive that far! Keep an eye out for when they open!

Where: 9050 Bramalea Rd, Brampton, ON, L6S 6G7.

When: opening soon! 

Price: $$.

Visit their website for more information!

Want to be the first to know about the hottest events in Toronto? Get first access to exclusive offers, deals, and giveaways in #the6ix? Sign up for our exclusive VIP list today and you’ll get the first-class treatment that only our VIPs get! 

Make sure to scroll down and sign up for our newsletter so you never miss a thing and are up to date with the latest and greatest things to do in Toronto!

Do you want us to feature your business in our “things to do” collections or its own post? Fill out the contact us form!

Latest POSTS