Few people make their mark in their country, let alone the world, but businessman and Shark Tank star Kevin O'Leary came, saw, and conquered in style. "As an investor I travel extensively in pursuit of opportunities," shares O'Leary. And those travels have taken the discerning O'Leary across the globe in search of gastronomic excellence. "Experience has taught me that while every deal looks good on paper, you only get the truth when you show up in person [and] one tactic I have found to be productive is to take the executives of a potential deal out for dinner and ply them with spectacular wines and great food." For O'Leary it's only at mealtime does the truth come out and guards are lowered. "As result I have built up a roster of great dining establishments in almost every major city on earth," adds O'Leary.
With that in mind, we tasked O'Leary with opening up his address book in Toronto. "Few people are aware that Toronto is the fourth largest city in North America," says O'Leary. "It’s Canada’s largest city and a cultural melting pot, so there are hundreds of great restaurants."
Below, check out O'Leary's favorite spots and make sure to check out more insights from our Inspectors, chefs, and celebrities.
Perhaps the best fine dining experience in Toronto. This restaurant has won countless awards including a MICHELIN Star, one of the few establishments in Canada to do so. I loved the seared Québec Muscovy Duck Breast with pomegranate sauce and the ravioli stuffed with pheasant along with roasted eggplant. Needless to say, the food and service is world class but it’s the venue itself that makes this a must-do. The dining room is located on the 38th floor of #1 Harbour Castle Square in downtown Toronto. There are stunning 360 views of the city—at night the skyline sparkles like diamonds. Plan on a two-and-a-half hour dining experience that you’ll never forget.
The One Restaurant at The Hazelton Hotel Toronto in Yorkville
Another Toronto standard. There are so many signature dishes, but one stands above all: the lobster spoons doused in melted butter. I bet you can’t just eat one. There is no better place to people-watch than from the corner table on the outdoor patio.. I have closed so many deals at that table that I have become superstitious. If I’m in Toronto to do business, I do it there with two orders of lobster spoons and a bottle of crisp Puligny-Montrachet. It always works—it's just good karma!
Sotto Sotto on Avenue Road
I have been going to this establishment for over 35 years. It’s a Toronto institution because of the consistency of its authentic Italian cuisine. Every dish is prepared in the classic, old-world way. The pasta is al dente to perfection, the fish are prepared Mediterranean style with lemon and olive oil, and the osso buco makes grown men weep. It is so succulent. I use my fingers, grab the bone, and suck out the marrow. Always finish with some grappa and the tiramisu for dessert. During the Toronto Film Festival in September, you will find some of the world's biggest stars dining there.
Blue Bovine
Blue Bovine is a steak and sushi house extraordinaire—it's my favorite restaurant in Toronto. Why? The food is spectacular and it’s right downtown inside of the historic Union Station that just underwent a $1.5 billion renovation. It’s attached via the indoors to Scotia Bank Arena which has 273 different events a year, so if you are going to a concert or a Maple Leaf or Raptors game, you can dine there first and go back for a nightcap afterwards without even having to walk outside.
I love this place so much that I became an owner—I just had to have a piece of the action. I always order the same thing: to start, a seafood tower with fresh king crab, lobster, jumbo prawns, oysters and salmon crudo, and a platter of hand-rolled Sushi. Then we move to the giant 44oz Australian wagyu tomahawk that rolls up to the table engulfed in Hennessy flames before it’s sliced by the server right onto your plate. Stop the madness! I invite my guests to order the duck fat hand-cut fries or the lobster mac and cheese and we enjoy the whole feast family-style.
The sommelier there is a wizard she has a photographic memory of every bottle in the cellar. Most athletes and artists that play in the arena stay close to Blue Bovine so it's not uncommon to see them at the bar after the big event.
Hero image: kevinoleary.com / Kevin O'Leary
