Activities + Things To Do,

Itineraries

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January 22, 2026

6 Unforgettable Things To Do This Valentine's Weekend

Make this Valentine’s Day one to remember with these 6 unique date ideas. From romantic strolls and artistic exhibitions to lakeside dining and foodie experiences, Toronto's harbourfront offers plenty of ways to make this year's Valentine's Day special.

With Family Day adding an extra day to this year's Valentine’s weekend, there’s even more time to spend with that special someone.

Your Guide to Valentine’s Day in Toronto:​

Free Hot Chocolate and Ice Skating at Sherbourne Commons

Kick off your Valentine’s weekend with a classic winter date at Sherbourne Commons outdoor ice rink, located at 5 Lower Sherbourne St.

Free skate rentals will be available on February 13 from 2 to 6 PM, making it a perfect daytime activity. Skating aids and helmets are also available to rent — for free!

Warm up with a free cup of hot chocolate and visit with MP Chi Nguyen.

The skating rink is just steps away from two beautiful lakeside restaurants - ideal for a romantic date.

Make a reservation at SIMONA, a delicious Mediterranean Italian restaurant with a cozy interior. SIMONA is less than a minute's walk from Sherbourne Common.

Or check out IRENE, a culinary classic with a dedicated Valentine's Day menu.

The Power Plant Contemporary Art Gallery

Take your date to The Power Plant Art Gallery this Valentine’s Day. Stroll hand-in-hand through thought-provoking art exhibitions from artists Jeneen Frei Njootli and Lucy Raven

The Power Plant offers free admission, and is located right on Toronto's waterfront at 231 Queens Quay W.

DJ Skate Nights at Harbourfront Centre

Don’t miss the final DJ Skate Night of the year at Harbourfront Centre! From 8 PM to 10 PM on February 14, enjoy beats spun by DJ Soul Kitchen while you skate the night away.

Free skate rentals are available, so you and your date can hit the ice without any hassle.

Learn more about Harbourfront Centre’s DJ Skate Nights here.

Comedy Show at Second City

Get ready for a night of laughter by taking your date to Second City’s Valentine’s special, Swipes Right: Hard Launch. The 90-minute comedy show hilariously explores the realities of modern dating.

Afterward, wrap up the evening at their onsite restaurant and bar, The Bentwood, with a view of Love Park’s heart-shaped pond.

Valentine's Day Special: Sean Jones

A Valentine’s Day special! Joined by guest performers and his stellar ten-piece band, Sean Jones delivers classic and original love songs to set the mood.

Don’t miss the one-time show on Saturday, February 14 from 8 PM - 12AM

Lakeside Dining On Valentine's Day

Toronto’s waterfront is home to some of the city’s best dining spots that offer something for every budget and taste.

IRENE | 25 Dockside Dr

IRENE is a known culinary classic, offering diverse cuisines and delicious meals.

IRENE has a dedicated Valentine's Day menu (available all weekend long), and a gorgeous interior. Perfect for your Valentine.

Miku | 10 Bay ST

Miku is an award-winning restaurant, known for specializing in Aburi cuisine.

Miku blends together Japanese culinary traditions with local ingredients, offering an unforgettable dining experience.

And on February 14 + 15, diners can enjoy a romantic Valentine’s Day menu featuring:

  • Exquisite 6-course kaiseki tasting menu

  • Live jazz trio (February 14 only)

  • Flavourful cocktails

Don Alfonso | 1 Harbour Square

For a truly unforgettable dining experience, book a reservation at the city’s most internationally acclaimed restaurant. This Michelin-star restaurant has also been named the second-best Italian restaurant in the world.

The delicious cuisine is paired with stunning views of the city skyline and Toronto’s harbour.

Happy Valentine's Day

From romantic strolls and artistic exhibitions to lakeside dining and foodie experiences, the Waterfront offers plenty of ways to make this year's Valentine's celebrations special.