Coolest neighbourhoods in Toronto: the ultimate area guide

Planning a working holiday in Canada? Gail, local Torontonian, guides us through the coolest neighbourhoods in Toronto, including some lesser-known local favourites.

Hello! I'm Gail and I want to show you around my amazing home town. As one of the most multicultural cities in the world, Toronto is full of incredible culture, food and people. It's home to large tech businesses, tourist attractions like the CN tower, and iconic sports teams like The Blue Jays (baseball), Maple Leafs (hockey) and the Raptors (basketball). And the rapper Drake of course. But Toronto is so much more than what you see on your screens.

From the independent boutiques and late-night bars of Dundas West to the vintage shops of Kensington Market and the beaches of the Toronto Islands, here is my inside scoop on best neighbourhoods to visit when in Toronto.

1. Dundas West: independent shops, restaurants and nightlife
2. Queen West and Parkdale: shopping, parks, bars and food
3. Kensington Market: vintage shopping, street art and diverse food
4. Toronto Islands: beaches, cycling and outdoor escapes

Dundas West: independent shops, food and nightlife

Dundas West, also known as ‘Little Portugal’, is a personal fave. This neighbourhood is full of quirky independent boutiques and places to eat and drink, making it a buzzy spot with locals, come day or night.

Where to shop in Dundas West

Take a stroll along Ossington Ave and shop-hop the cute independent clothing, decor and homeware stores. Easy Tiger and Rose City Goods are great places to get an ethically-sourced gift (for you or a mate).

Best places to eat and drink in Dundas West

Hungry? Get a grab-and-go lunch at Lambo’s deli where you’ll find next-level modern Italian deli sandwiches. For dinner or afternoon drinks, Manita is a personal favourite – a street corner sidewalk patio lined with french-style cafe tables. So you can sip on a drink, enjoy some food and watch the cool kids walk by. If you’re ready to call it a night, stop by Bang Bang ice cream on your way home for original flavours like ‘cinnamon toast’ to try.

Best late night spots in Dundas West

For the night owls - you’re in the right place. Dundas West is a great spot for a fun night out, with Churchill’s, Mahjong Bar, Get Well, Bambi’s, The Painted Lady or Sweaty Betty’s all great for a boogie. If you need a midnight snack and a debrief after – Lakeview Diner has some tasty diner classics (and they close at 4:00am).

Queen West and Parkdale: shopping, parks and bars

Just a short walk away and you’ll find yourself in the Queen West & Parkdale area. Home to Trinity Bellwoods park, TV chef Matty Matheson’s signature smash burger and cool stores that will make your purse twitch.

Things to do around Queen Street West

Start your day off with a seriously good coffee at Sam James, or if it’s a nice day, sit in the beautiful back garden at Cafe 23. Walk along my favourite shopping street Queen Street West and window shop at Gravity Pope and Tusk full of unique knick-knacks and cool clothing. Trinity Bellwoods Park is where the locals love to spend an afternoon or evening hanging out, listening to music and enjoying a picnic with some (actually legal) beers.

Where to eat and drink around Trinity Bellwoods

For a vibey lunch or dinner, Terroni does some delicious Italian food with lots of vegan and gluten-free options. 416 Snack Bar, North of Brooklyn Pizza and The Burger’s Priest are some other tasty spots to enjoy in the area.

For a drink with a difference, escape to the dimly lit Shameful Tiki Room, where the staff come out chanting and singing with smokey dry ice-topped drinks. Other night-out favourites are Apartment 200 or Dog & Bear.

Kensington Market: vintage shopping and global food

Kensington Market is a bohemian neighbourhood full of character, community and culture. Many locals have been here since the 70s, now living side by side with Toronto's university students. The cultural and ethnic diversity make this area one of the best spots for a foodie night out!

Best Vintage Shops and Independent Stores

For the thrifters, Kensington Market is arguably the best place in Toronto for vintage shopping, with tons of eclectic second-hand stores to browse. Courage My Love, Flamingo Vintage and Public Butter all offer bargains in vintage clothing and knickknacks.

Where to Eat in Kensington Market

Get your vitamins in smoothie form and pick up some plants to decorate your room at The Organic Press. If you're in the mood for something sweet, head into vegan and gluten-free-friendly Bunners for thick soft serve ice cream, tasty cupcake flavours, or a giant glazed cinnamon bun drool. Still hungry? Impressive. I’m a big fan of El Rey, a Mexican restaurant with killer tacos, mezcal-based drinks and a vibrant atmosphere to soak up.

Going out in Kensington Market

Time to show off your moves. For those who want to keep the night rolling check out live music at Supermarket or Handlebar. Just around the corner in Little Italy is Sneaky Dee’s, where you can enjoy cheap cheesy nachos and dance your heart out at this casual Toronto institution.

Toronto Islands: beaches, cycling and summer days

If you’re here in Summer, Toronto Island is an absolute must. Just south of the city, the island beaches feel like an oasis of calm, well worth the short ferry ride.

Best beaches on the Toronto Islands

To explore the beaches and soak up the sea air, rent a bike. Pack a picnic and park up for the day at Gibraltar Point Beach which, in my humble opinion, is one of the nicest and most relaxing beaches to spend the day at. Ward’s Island Beach is another smaller and more relaxed beach, near cafes, cottages and the ferry dock.

Hanlan’s point is a clothing-optional beach that can get busy in the summer with a really fun and sociable atmosphere. In peak summer it often turns into a little beach party on Friday or Saturday evenings, where people bring their own drinks and music – it can get a bit rowdy but in the best way possible. There’s even a festival called Electric Island here in the summer months with a couple of different stages and genres to get groovy to.

Forgot your packed lunch? It happens. There are a few places to eat on the island – The Riviera and The Island Cafe, both offering casual pub-style food and drinks to watch the sun go down with.

How to get to the Toronto Islands

The islands are easily accessible via a 10-15 minute ferry from Jack Layton Ferry Terminal, just 10 minutes south from Union Station. And make sure you check the time of the last ferry home and ticket information – you don't want to get stuck there until the morning. Or maybe you do?

Planning a working holiday in Canada?

Our Work Canada program includes the option to pre-arrange a 4-6 month summer or winter season job, arrival accommodation and help sorting all the boring bits – such as tax and bank accounts. Bear spray not included.