Make Toronto Your Next Long-Weekend Getaway — No, Really, I’m Serious

There's always something to do in Toronto.
Publish date:
May 20, 2016
vacation, tourism, Canada

Whether you're looking for a quick getaway or a full week's vacation, there's never been a better time to put Toronto on your list. From brunch o'clock until last call, Drake's The 6ix is one of the hottest places to be. The sluggish Canadian dollar makes TO a great choice for Canucks wanting to avoid expensive travel to the US and Europe and for the rest of the world looking for an excuse to party in Canada, well, it's as if everything's on sale.

Consistently rated one of the world's most liveable spots, Toronto is the 5th largest city in North America. Bigger than Chicago, it's the 4th most populous after Mexico City, New York and LA. It's a boom town where the number of skyscrapers has tripled in the last 9 years. An ongoing architectural renaissance has seen the creation and transformation of some of the city's most important artistic spaces under the guidance of big name architects.

With 50 percent of its population born outside of Canada, Toronto is one of the most multicultural cities in the world. It's home to 200 distinct ethnic groups which means you've got more options here than at Epcot's World Showcase. You want late night Ethiopian food? No problem. Karaoke in Koreatown? Sing your heart out and recover over dim sum the next day. The GTA has not one, but six Chinatowns and one of the largest in North America.

Toronto is hot. Literally. Contrary to rumors, it's not always winter here and summer temps can exceed 40 degrees Celsius (that's 104 Fahrenheit, my Yankee friends) which makes summer a great time to visit when the Tdot is buzzing with outdoor parties. The city draws international crowds for annual festivals like Caribana, a massive salute to Caribbean culture that includes one helluva street party, a parade and Drake's OVO festival. Taste of the Danforth shuts down all of Greek town to celebrate Toronto's multicultural diversity and Afrofest showcases the best in African music, art, culture and food. Toronto Pride Week is such a big deal here that, this year, we decided to give it a whole month.

There's always something to do in Toronto. We're a die hard hockey town that's also bursting with pride over our baseball and basketball teams. We've got world class opera and ballet and the Theatre District is the world's largest after New York's Broadway and London's West End. If throwing axes or chilling at a cat café are more your jam, we've got that too. Here's what else you need to know:

Hip Hotels

If you're fancy, the Royal York and the Windsor Arms are where you'll wanna be. But the cool kids stay at The Drake (no relation to our hometown) or the Gladstone where its contemporary artist designed rooms are juxtaposed against the architecture of the 1889 building. Located in the city's most creative neighborhood, this boutique art hotel has 3 gallery spaces and dozens of art exhibits every year.


High end fashion abounds in trendy Yorkville but locals know the real scene is on West Queen West. Vogue magazine knows it too because they named the district from Bathurst Street to Gladstone Ave the coolest neighborhood on the planet. Well, almost. Vogue actually ranked it second after Tokyo's Shimokitazawa. It's the perfect place for wandering in and out of indie clothing shops, design and antiques stores, French patisseries, art galleries and cafés. It's where you'll find the street art of Graffiti Alley and where you're most likely to be accosted by a fashion blogger and asked for a pic.

The Museums are Cool

We have a museum that's just for shoes. From Chinese bound foot shoes to Carrie Bradshaw's Blahnik's, the Bata Shoe Museum displays an impressive collection of what we've been putting on our feet for the past 4500 years.

The TIFF Bell Lightbox, home to the Toronto International Film Festival is a cinema complex featuring curated programming, and a cultural center that includes a reference library, student spaces, restaurants, a rooftop terrace and galleries showcasing temporary film related exhibitions covering subjects like the works of Tim Burton, David Cronenberg, Grace Kelly and Fellini.

The Royal Ontario Museum is home to an important collection of world art and natural history. The museum's 2007 Deconstructionist crystalline expansion (by superstar architect Daniel Libeskind, no less) against the original 1914 heritage building, continues to be a source of local controversy. Critics have called it 'oppressive, angsty and hellish' and one of the 'ten ugliest buildings in the world.' We can't agree, but people are talking. Kids know the ROM as the place to see dinosaurs but until September 5th, it will also host Tattoos: Ritual. Identity. Obsession. Art. An exhibit about, you guessed it, tattoos. Share your own body art using #ROMink for a chance to be included in this badass show.


Toronto loves its markets. The historic St. Lawrence has been feeding Torontonians since 1803 and is its most famous. But my favorite is The Stop at Wychwood Barns. The airy brick structure with steel interiors is a heritage building and former streetcar maintenance facility built in 1913 that now contains artist studios. It has an outdoor Saturday morning market featuring local, sustainable organic and artisanal products with live music, park space, beach volleyball and a wading pool for kids.

You might remember the Distillery District from the film Tommy Boy. The former Gooderham and Worts distillery has been converted into a pedestrian complex of studios, shops, galleries, restaurants and theaters. In November and December it hosts a European style Christmas market.

And a trip to Toronto wouldn't be complete without at least a few hours spent wandering around Kensington Market, an eclectic neighborhood of creatives and writers, produce stalls and bakeries, ethnic street foods and indy bookstores where Trotskyists can sometimes be spotted handing out pamphlets. Get there soon before the area gets gentrified.


We have one. In the middle of the city sits Gothic Revival style Casa Loma. Okay, technically 'casa' means house, but close enough. Built by Henry Pellatt in 1911 and later seized by the city for a whole tax thing, today it's a popular spot for movie shoots, weddings and selfies.


There's a lively comedy scene in Toronto where sketch and improv loom large and Montreal's Just For Laughs festival is a recent import. Toronto was a launching pad for such giants as John Candy, Martin Short, Mike Myers, Lorne Michaels and many, many others. If you aren't watching Schitt's Creek yet, you should be. When in town catch a show at the Second City MainStage or take a drop-in improv class at the newly renovated and super slick training center. Or see one of the many smaller shows at great venues like BadDog, Comedy Bar and Social Capital Theatre. If you see Mantown on the lineup, get there early and warn your date that you might squirt beer out your nose.

If you're still reading this you might have guessed that Torontonians (me!) are known for having an obnoxious amount of civic pride, but can you blame us? Toronto is great! Toronto has so much more to offer that I couldn't possibly cover it all here and sometimes the best travel experiences are the discoveries we make ourselves. We hope you'll come and see for yourself soon.