Great Dates in 50 States (and Canada!): Toronto, Ontario

(e’s note:  Please welcome today’s guest writer for Great Dates in 50 States – and Canada!,  the guy who can kick your butt into making the changes needed for you to succeed, Alex Fayle of Someday Syndrome.)

When most people think of a date in a large metropolitan city like Toronto, they think nightclubbing, dinner in fancy or chic restaurants, or going to the theater, however Toronto has a lot more to offer, from discovering Toronto’s extensive park systems, to exploring the city’s culturally diverse neighborhoods.

Toronto Island

[Great photo by Jane Chu on]Although most people in Toronto know that Toronto Island exists, very few actually go there. The waterfront is separated from the rest of the city by highways and railway tracks but once you get down to the bottom of Bay Street, it’s just a short ferry ride across to the Island that can occupy a full day or more.

To explore the whole island, a pair of bicycles works best, and if you don’t have any, you can rent them on the Island at the main ferry port on Centre Island. They even have carriage style pedal bikes allowing you to sit side by side as you explore the island.

If you’re in a childish mood, buy a few tickets and check out Centreville, the island’s small amusement park, including a Ferris wheel, bumper cars and a waterlog ride.

Taking your bicycle over the bridge and heading east you’ll pass a church where you can picture getting married in (if your date’s going really well) and then ride on to Ward’s Island, where you can wander through the streets of the cottage style homes, many with highly interesting architectural details and innovations.

On the way back from Ward’s Island, make sure you stop in at the Rectory Café for lunch. The best food on the island for sure.

After lunch, take the south boardwalk path west all the way along to Hanlan’s Point which boasts Toronto’s only official nudist beach. Discover just how liberated your date is with a suggestion of a visit.

If you’re on foot or using your own bikes, you can then return to the mainland from the ferry at Hanlan’s Point, or return to Centre Island and take the ferry from there.

A map plus a list of ferry times, activities and even Bed & Breakfasts (if the date goes THAT well) can be found on the Toronto Island Community website.

Distillery District

[photo by IpKang on]A former industrial wasteland used primarily for filming period movies and TV shows (like Chicago and Road to Avonlea) the Distillery District has converted itself into one of Toronto’s hottest artist neighbourhoods. With galleries, museums, cafes, restaurants and artisan shops like fresh French bakeries there’s plenty to do as you chat and get to know each other better.

The Distillery District is also only a few blocks from the old part of the city, where you have the opera, stage and dance theatres, jazz clubs and the St. Lawrence Market (for those who want to buy fresh produce and take it home for a intimate dinner for two).

Check out all that the Distillery District has to offer on its website.

Kensington Market

[photo by Rich Kang on]Kensington Market has been the home of an eclectic mix of cultures for over a hundred years. It’s managed to resist much of the gentrification that has hit the rest of the city and so its used clothing shops, fresh fruit, meat and fish markets, and Toronto Fusion cuisine from the dirt cheap to the highly expensive all find a home in this world-renowned section of Toronto.

Smack dab in Toronto’s Chinatown, if you visit Kensington, you’ll also be able to sample some of the best Asian culture that exists in North America.

Visit the Kensington Market website for more details.

Toronto Parks

[photo of High Park by Free Flower on]If nature’s your thing, then the Toronto Parks system is a nature lover’s dream. From High Park to the Belt Line Trail to the Rouge Valley trail system, no matter where you are in Toronto, you can find a quiet piece of green to get lost in.

And with all of these parks you don’t even have to wait for warm weather to explore. Toronto, being a winter city, has outdoor events in many of its parks all year round, including tobogganing, cross-country skiing, and ice-skating.

Check out the full cycling and hiking maps on the City of Toronto website.

West Queen West

[Photo of the Drake Hotel by 416Style on]For the hippest of the hippest in the city, the current hot spot is over on West Queen West, with the Drake and the Gladstone Hotels. Sitting on the edge of Parkdale in a formerly no-man’s-land the conversion of these two hotels hyper-cool night spots has transformed this strip into the place to go for a night out. Of course you can start a little farther east at Spadina and work your way down the whole list of bars and clubs like the Horseshoe Tavern for live music, the Bovine for some rockin’ beats, the LeVack Block at Ossington for a late snack and then end the night at the Drake or the Gladstone.

Check out BlogTO’s description of the whole West Queen West strip.

Fran’s Diner

[Photo of sign by Destang on]Open since the 1940s, Fran’s Diner on College Street at Yonge is perfect for an after-hours chow-down. The menu serves breakfast, lunch and dinner at all hours of the day, meaning you can have whatever tickles your fancy.

You’ll likely have a wait, but if the date’s going well, this will just be another excuse not to separate. The booths offer privacy despite the neon-bright lighting and sampling from each other’s plates is a super way to up the connectivity that’s building.

Visit Fran’s website for more details.

For more in general about Toronto nightlife, restaurants and neighbourhoods, visit which has extensive series of guides to all things Toronto.

Although Alex still loves Toronto, he no longer lives there. In 2006, he followed his dream of writing to northern Spain, where he teaches others to follow their own dreams through Someday Syndrome. People who want make the big changes in their lives often don’t know exactly what it is they want or how to get started. Alex helps clear out the mental, emotional and physical clutter that block people from following their dreams and curing themselves of Someday Syndrome. Check out the blog and coaching services at

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