How To Have A Magical, Romantic Christmas Weekend In Toronto


There’s always an extra level of romance during the holiday season, and Toronto has an endless supply of romantic and festive ways to celebrate. From delicious holiday dining experiences, to cozy Christmas themed cocktail bars, and skate date nights under the stars, discover the charm of Canada’s largest city this holiday season. Check out our guide for all the best ways to have a magical, romantic Christmas weekend in Toronto.

Romantic Holiday Retreats

Check-in to one of Toronto’s most luxurious hotels complete with stunning festive decor, perfect for that ultimate couple holiday selfie! These stays offer the best amenities, boozy pop-up bars, festive dining and holiday inspired afternoon teas.

PC: Fairmont Hotels / Accor

Have A Romantic Holiday Inspired Evening At Fairmont Royal York

Experience the grandest of holiday feelings with festive dining and entertainment offerings at Toronto’s landmark hotel. From an annual tree lighting ceremony with a festive window display reveal, to holiday afternoon tea and festive dining, it’s the perfect romantic holiday retreat.

PC: Shangri-La Hotel

Cozy Up By The Fire & Listen To Christmas Carols At Shangri-La Hotel

Celebrate the festive season at one of Toronto’s favorite hotels. Share a romantic moment while sipping a cocktail by the fireplace in the lobby or enjoy the hotel’s popular Nutcracker High Tea while listening to Christmas carols being played on their custom Fazioli piano.

Step Into A Historical Holiday Romance

Looking to explore? Step into your own holiday romance while doing some last minute high-end shopping in Yorkville, a charming 19th century village nestled in the heart of Toronto. For a touch of European holiday glamour, stroll the cobblestone streets under a canopy of lights at The Distillery Winter Village.

PC: Tiffany Shum / Harlton Empire

Create Your Own Magical Holiday Romance In Yorkville

Throughout November and December, the Bloor-Yorkville area celebrates the holiday season by illuminating the neighborhood with a one-of-a-kind display of festive lighting. Couples 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.

PC: Distillery Winter Village

Stroll Cobblestone Streets At The Distillery Winter Village

Amongst The Distillery Historic District’s 65+ local shops, restaurants and cafés, you’ll find outdoor Distillery Winter Village vendor cabins offering specially curated seasonal items, gifts and can’t-miss delicious food cabins. Enjoy strolling the cobblestone streets under the canopy lights while you select the perfect gift for that special someone.

Cozy Up With A Christmas Cocktail

Cozy up for a Christmas cocktail at one of Toronto’s many holiday themed bars. Filled with twinkling lights, kitschy décor and festive drinks, it’s the best way to warm up after an afternoon of romance and adventure.

PC: Tiffany Shum / Harlton Empire

Have A Nostalgia Filled Date At Miracle Toronto

An instant holiday tradition since coming to Toronto in 2018, Miracle is a Christmas-themed pop-up cocktail bar that serves holiday cocktails in a festive setting. With kitschy holiday décor, cocktails by the team at Civil Liberties, and the nostalgic energy of the best office party you’ve ever been to, Miracle is sure to get even the grouchiest grinch in the holiday spirit.

PC: Tiffany Shum / Harlton Empire

Celebrate At The Thirsty Elf Christmas Cocktail Bar

The Fairmont Royal York has been serving Christmas themed cocktails at their holiday pop-up bar “The Thirsty Elf“ for a few years now. Covered in holiday decor and playing all your favorite Christmas songs, it’s the perfect way to make your spirits bright, and the perfect time to get cozy and close with your loved one.

Skate Under The Stars

An evening under the stars is the perfect way to end your romantic getaway. For the perfect Toronto photo op, head to Nathan Phillips Square. Or for something a little more intimate head to Union Station’s rink for a skating date with skyline views.

PC: Tiffany Shum / Harlton Empire

Share A Perfect Toronto Photo-Op At Nathan Phillips Square

Get in some holiday shopping at the Eaton Centre, and then head to Nathan Phillip’s Square for a magical skate under falling snowflakes and a twinkling canopy of lights. Don’t forget to take the ultimate couple’s selfie in front of the famous Toronto sign.

PC: Tiffany Shum / Harlton Empire

Glide Hand-In-Hand & Take In Skyline Views At Union Station

Directly across from Fairmont Royal York, you’ll find the Union Station Holiday Skating Rink. A little more intimate, they offer free skate rentals and welcome all levels. Glide hand-in-hand under the Toronto skyline and warm up after with a drink at The Thirsty Elf.

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