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  • Writer's pictureJared Cotta

Explore Toronto with Simon and the Cotta Brothers

Simon Cummings was an amazing guest and taught us everything we needed to know to have an awesome trip to Toronto. The city has been on the rise for a long time according to Simon, well before the Raptors won the NBA Finals. Toronto is a melting pot with tons of cultures on display and its an absolute haven for foodies. We'll likely come back with more lists of eateries as soon was we can go visit but for now you can check out the activities Simon put on our list when we visit this Canadian metropolis.


Ossington - Commonly known as Ossington Strip, this popular neighborhood spans along Ossington Avenue near downtown Toronto. This street is packed with some of the newest and best bars and restaurants in the city!

King West - the main commercial thoroughfare of downtown Toronto, home to some of Toronto’s most popular bars and restaurants


Poutine - French Fries, cheese curds, hot gravy, it's that simple. You can find it all over the place and its a national treasure.

Terroni - With three locations throughout Toronto, this popular Italian restaurant is a local favorite, offering classic dishes and a fine dining atmosphere. Terroni’s is the great place to have a nice dinner before going out in Toronto’s exciting downtown.

Simon’s Recommendation - Try the truffle mac n cheese!

57 Adelaide St E, Toronto, ON M5C 1K6, Canada

Chris Jerk - The healthier of the two Jamaican restaurants frequented by our guest, this hole in the wall eatery is a real hidden gem in the city. Chris Jerk offers Jamaican classics and a hole-in-the-wall atmosphere, it’s a must hit for anyone looking for a quick, flavorful bite near Leacock.

2570 Birchmount Rd, Scarborough, ON M1T 2M5, Canada

Jamaica Stamps - If you’re looking for delicious, authentic Jamaican cuisine that’ll stick to your ribs and make you fill you up, Stamps is the place for you. One of Simon’s favorite spots for jerk chicken, this local eatery is fast and affordable with great Caribbean flavor.

1053 Midland Ave, Scarborough, ON M1K 4G8, Canada

Bahn Mi Boys - This joint is often lauded as one of the best places to grab a Bahn Mi in the city. It wasn't directly recommend by Simon but we know he loves Vietnamese food so we think he'd approve. Bahn Mi has popped up multiple times on the show! This place is authentic and delicious

Couple Locations but try 392 Queen St W, Toronto, ON M5V 2A9, Canada

Regulars Bar

Drinks / Nightlife

Lost and Found - This popular basement night club can be found in the Toronto Fashion District and is a favorite of celebrities visiting the city. If you are looking for that star treatment and want to throw down in the best club in the city, you got to hit Lost and Found. It's the place to be seen.

577 King St W, Toronto, ON M5V 1M1, Canada

The Bisha Hotel - This luxury hotel found in downtown Toronto boasts a rooftop bar and restaurant with an unforgettable view of the city. If you’re looking to start your night off with a drink at a high end bar, you can’t do much better than Kost on the 44th floor of the Bisha.

80 Blue Jays Way, Toronto, ON M5V 2G3, Canada

Door Three - This fashion district nightclub has an energetic party atmosphere, bottle service, and a stunning view from their rooftop. Obviously you must plan your trip in the summer if you want to enjoy these roofs but if you make it to the city check them out!

667 King St W #2, Toronto, ON M5V 1M9, Canada

Sneaky Dee’s - A must-hit local haunt in Little Italy, this hole-in-the-wall dive bar is a bar, live music venue, and tex-mex restaurant, what more could you possibly ask for from a night out! Sneaky Dee's is popular with the university crowd but it offers fun times for any dive bar enthusiast.

431 College St, Toronto, ON M5T 1T1, Canada

Regular’s - If you’re looking for a great late night spot for drinks and food, look no further than Regular’s. Conveniently located in the Fashion District, this bar offers great bar food and creative cocktails. Their menu is inspired by the diversity of the city.

668 King St W, Toronto, ON M5V 1M7, Canada


CN Tower - At over 1800 feet high, this observation tower on Toronto’s bayfront is the tallest free-standing structures in the Western Hemisphere. This soaring landmark offers a breathtaking panoramic view of downtown and beyond. The iconic tower is the centerpiece of this beautiful city's skyline so you can't help but appreciate it.

290 Bremner Blvd, Toronto, ON M5V 3L9, Canada

Caribana - This celebration of Caribbean culture takes place every summer and claims to be North America’s Largest Street Festival. You won't be able to stop dancing once the sounds of soca music fills the air. Caribana offers everything from parades to pool parties, you’ll definitely want to reserve your hotel and tickets in well in advance for 2021.

Check website for exact 2021 dates.

Ripley’s Aquarium of Canada - Just a one minute walk from CN Tower, this massive aquarium is home to thousands of different species of sea creature. It’s a must-hit for anyone exploring Old Toronto. Simon adds a disclaimer: he has never actually visited this spot but its popular.

288 Bremner Blvd, Toronto, ON M5V 3L9, Canada

Nature and Excursions

Toronto Island Park - Just a short ferry ride off the mainland, Toronto Island Park is an amazing place to soak up some sun. With beaches, parks, nature paths, and even a children’s amusement park, there’s truly something for anyone looking to spend some of their trip in the great outdoors.

Scarborough Bluffs - Composed of nine parks in the Scarborough district, The Bluffs are a uniquely beautiful feature of the Toronto Coastline. With plenty of walking/running trails and scenic lookout points, it’s well worth the drive to these cliffside parks located just outside the main city.

As you can see Toronto is an amazing city filled with food, fun, and activities. What makes this city special is how it melts so many cultures into one destination without rejecting any groups' unique characteristics. Toronto is a celebration of diversity. It is a city on the rise as Simon says, and it looks like there is no way it is slowing down. If you are planning a trip to Toronto we hope you will find this article helpful.

Don't forget we can't make the Cotta Brothers Travel Club without our amazing guests. If you are passionate about another Canadian city or any destination in the world, please reach out and lets do and episode together! Check out our contact page!

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