Hy's Steakhouse & Cocktail Bar

Stepping into Hy’s on Bay Street feels like entering a different era of Toronto’s Financial District. Housed in a grand, former bank building, the space is a masterclass in moody, upscale atmosphere, featuring rich mahogany, plush leather booths, and a dramatic 35-foot wraparound bar that anchors the main floor. Founded by Hy Aisenstat in 1955, the brand has become a Canadian institution, and this location perfectly balances that storied, old-school steakhouse gravitas with a modern, polished edge. It is the kind of place where the lighting is low, the service is impeccably professional, and you feel entirely insulated from the frantic pace of the surrounding office towers, making it a go-to for high-stakes business deals or a celebratory night out.

For a first-timer, the experience isn't complete without the theatre of tableside service; the Caesar salad prepared right before your eyes is a non-negotiable starter. Follow that with their signature Canada Prime steaks, which are consistently aged and grilled to perfection. Don't skip the famous cheese toast—it’s a cult classic for a reason. Expect a high price point, as this is fine dining, so reservations are highly recommended, especially for prime evening slots. If you’re looking for a slightly more relaxed vibe, aim for their daily happy hour in the lounge, which is one of the best in the area for a well-made, ice-cold martini and a more accessible taste of the menu.