A couple looks at the Toronto skyline from the gardens of Casa Loma

DATE TIME

2 night/ 3 day itinerary

Whether you need a break from the little ones, the home office or just want some quality time together as a couple, Toronto has everything you need to reconnect--and have fun!

A couple in a restaurant on a date

Day 1

Afternoon

Start your Toronto sojourn by exploring a neighbourhood. People-watch and vintage shop in funky Kensington Market or park yourself on a patio (Sassafraz is ideal) and watch fancy cars cruise by in higher end Yorkville or take your pick of ‘hoods.

Evening

It’s time to chill out and gaze into each other's eyes over a delicious cocktail and meal with these top picks for date night. After, go for a pub crawl and sample local craft brews at these lively pubs before calling it a night.

The love locks art installation at the Distillery District
The love locks art installation at the Distillery District

Day 2

Morning

Start your day with a scenic coffee at a Harbourfront café (Boxcar Social is our pick) and perhaps squeeze in a free contemporary art exhibit at the Power Plant, before hopping the ferry to the Toronto Islands. There you can bike or walk to a secluded spot for a picnic, hit the beach (clothing optional or not!) or get refreshed at one of the casual cafés-with-a-view on Ward’s island. If you’re feeling more energetic, rent a kayak for a tranquil paddle à deux around the lagoon. 

Afternoon

If you love someone, let them go... shopping! The Eaton Centre is a mecca for top brands including iconic menswear retailer, Harry Rosen, and Queen West offers a mix of indie boutiques, familiar chain stores and hip galleries.

If an adrenaline fix is what you crave, the Jays, Toronto FC or any other big league team that’s in town for a day game, will get your heart pumping.

Evening

An evening in the Distillery Historic District gives you a ton of options. Take a Segway tour, see a Soulpepper play, pose with the LOVE art installation or simply stroll the cobblestone streets and enjoy the Victorian buildings filled with artisans, retailers and restaurants. For a classically romantic dinner spot, choose Cluny Bistro.

If you’re up for more fun, the Entertainment District is packed with musical theatre, dance clubs and live music options that will take you into the wee hours.

Scarborough Bluffs
Scarborough Bluffs

Day 3

Morning

If you have access to a car, a jaunt to the spectacular Scarborough Bluffs should be on your Toronto bucket list. Feast your eyes and fill your Instagram.
Still in the east end, but more accessible by transit, is the charming Beaches neighbourhood. Walk or bike along the boardwalk, catch a beach volleyball game or rent a stand-up paddle board.

Or, head west to Port Credit, a picturesque lakeside community located in Mississauga. Eat, shop and take in one of the many pop-up events happening year 'round.

Afternoon

There’s a reason the CN Tower is a popular pick for marriage proposals, so whether you’re popping the question or just celebrating being together, a trip up the iconic Tower is a must. Top off your holiday with a tour of Steamwhistle Brewery, housed in the historic Roundhouse train station. 

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