A couple walking down the platform at UP Union Station

Your Guide to the Best Valentine's Date In Toronto – Restaurants and Beyond

Published: February 9, 2024

In February, Toronto has a reputation for being a little cold.

The winter storms from Lake Ontario push the masses indoors, hibernating for the last little bit of winter before a magnificent Spring begins.

A cold February does not scream romance, but Valentine’s Day, February 14th, is the perfect opportunity to break away from the cold outside and embrace the warmth of each other's presence.

UP Express is Your Ticket To The Heart

Create the perfect date using UP Express with these recommendations, all within a close distance of our four (4) stations.

Toronto has a lot to offer the romantic. From award-winning restaurants to unique experiences only available in a city like Toronto, UP Express is truly your ticket to the heart.

Keeping it Classic: Best Date Restaurants in Toronto

One of the most popular ways to celebrate Valentine’s is by treating your significant other to a romantic dinner at one of Toronto's many incredible restaurants. From cozy bistros to elegant fine-dining establishments, the city has no shortage of options to suit any taste and budget.

Canoe Restaurant - 66 Wellington St W 54th floor, Toronto, ON M5K 1H6

Canoe restaurant located 54 floors above downtown Toronto

Located on the 54th floor of the TD Bank Tower, the restaurant offers breathtaking views of the city skyline from its floor-to-ceiling windows. The ambiance is cozy and intimate, with dim lighting and comfortable seating arrangements. The menu features Canadian-inspired dishes with a contemporary twist, using locally sourced ingredients that the restaurant's talented chefs expertly craft.

Hole In the Wall TO - 2867A Dundas St W, Toronto, ON M6P 1Y9

Hole In the Wall, a cozy venue for live music and craft beer in Toronto.

This unique space is wedged between two heritage buildings in Toronto’s up-and-coming neighbourhood, the Junction. Known for its extensive craft beer list and unique menu, the Hole In The Wall’s charm comes from its unique location, intimate lighting, and private nature, making it a great pick for a romantic Valentine’s Day dinner.

El Almacen Yerba Mate Café - 1917 Weston Rd, York, ON M9N 1W7

El Almacen Yerba Mate Café is a cozy and charming café in Toronto.

Nestled near Weston UP lies a hidden gem that will transport you to the romantic streets of Buenos Aires. El Almacen Yerba Mate Café is a cozy and charming café that serves the finest yerba mate and coffee from around the world, providing the perfect setting for a romantic outing.

Thinking outside the box: Best Date Ideas in Toronto

You're in luck if you're looking for date ideas in Toronto that go beyond the typical dinner and drinks. Toronto offers many unique and exciting activities for couples looking to switch their routine on this special occasion. From outdoor adventures to cultural experiences, there's something for everyone to enjoy.

Check out a comedy show at Second City - 1 York Street, 110 Harbour St, Toronto, ON M5J 0B6

Second City comedy show in Toronto.

If you're looking for a unique and entertaining Valentine's Day date idea in Toronto, why not check out a comedy show at Second City? With hilarious sketches and witty improvisation, Second City will surely have you and your significant other laughing all night. Plus, as a PRESTO Perk, PRESTO cardholders can get 10% off tickets to Second City shows. It's the perfect way to celebrate Valentine's Day with a little bit of laughter and fun.

Visit the aquarium, CN Tower, ROM or AGO

The underwater viewing tunnel at Ripley’s Aquarium of Canada is a must-see for Toronto visitors

You can't go wrong with a visit to the Ripley's Aquarium, CN Tower, ROM or AGO. These iconic Toronto attractions offer a range of exhibits and activities that are perfect for couples looking to bond over art, history, or nature. Whether you want to marvel at the deep-sea creatures at the aquarium, take in the city skyline from the CN Tower, or explore the galleries at the ROM or AGO, there's something for everyone to enjoy, all within walking distance of Union Station. Plus with PRESTO Perks, save 15% off CN Tower General Admission Timed Tickets or when you show your PRESTO card.

A romantic walk in the Distillery District - 55 Mill St, Toronto, ON M5A 3C4

snap pics with your sweetheart at The Distillery District Love Sign, made from many colourful locks

Transport back in time with a stroll through the Distillery District. The cobblestone streets, beautiful architecture, and charming atmosphere make it a picturesque location for a romantic walk. Plus, it's conveniently located just a short distance from Union Station, making it easily accessible via UP Express.

Warm Their Heart With a Drink: The Best Date Bars in Toronto

Looking for a romantic spot to enjoy a Valentine's Day nightcap with your significant other? Toronto has some of the best bars in the country that offer an intimate and cozy ambiance, perfect for a memorable date night. Whether you're in the mood for craft cocktails, fine wine, or local beer, these bars have got you covered.

Wine and paint at Pinot’s Palette: 2866 Dundas St W, Toronto, ON M6P 1Y8

Wine and paint night at Pinot's Palette in Toronto, ON.

A unique and creative way to celebrate Valentine's Day in Toronto is a wine and paint night at Pinot's Palette. Located close to Bloor UP, Pinot's Palette offers a fun and relaxed atmosphere where you and your significant other can create your masterpiece while enjoying a glass of wine. With talented instructors guiding you step-by-step, you don't have to be an artist to create a beautiful painting.

Grab a drink together at Bandit Brewery - 2125 Dundas St W, Toronto, ON M6R 1X1

Groups of people sitting outdoors dining under trees and string lights

For something more laid-back and low-key, why not head to Bandit Brewery for a craft beer on Valentine's Day? This cozy and intimate brewery offers a wide selection of locally brewed beers and ales and tasty bar snacks to nibble on while you enjoy your drinks. The covered outdoor patio provides a warm and welcoming atmosphere that is perfect for a casual date with your significant other.

Pearson and Beyond

No matter where you end up this Valentine's Day, with UP Express, you can rest assured your Valentine's Day starts on the right foot.

Give your significant other the world this Valentine's Day with a comfortable connection to Toronto Pearson International Airport using UP Express. Toronto Pearson is an international aviation hub and has links to many bucket list destinations.

Going on vacation over Valentine's Day is a perfect way to celebrate with your significant other. And what better way to start your romantic getaway than by taking UP Express to the airport? With UP Express, you can avoid the stress of driving and parking. Instead, enjoy a stress-free ride with your loved one, taking in the scenery and anticipating the adventures that await you both on your vacation.