Toronto has always been a great destination for celebrity spotting (hello, TIFF!), but it’s also a great place to get a bit of celebrity treatment. And what better place to get insider intel on the hottest spots in town than the hotel to the starts, the Four Seasons Toronto?
We asked the Four Seasons Toronto’s chief concierge, Harry Hollywood, for his expert recommendations on where to eat, drink and play in the city. And he has over thirteen years of luxury hospitality experience under his belt and is a member of Les Clefs d’Or Canada, so he’s got the inside track on everything. Here’s Hollywood’s short list.
Eat
Ristorante Sotto Sotto, 120 Avenue Road: “An undisputed Toronto landmark that serves as the city’s premier star-studded clubhouse,” Hollywood says. “It is renowned for its timeless Roman comfort food and an iconic ‘Wall of Fame’ that features decades of elite regulars, from legacy Hollywood actors to music icons like Drake.”
Joso’s, 202 Davenport Road: “A vibrant, multi-level monument to Mediterranean dining with deep roots in the entertainment industry,” Hollywood says. “The eclectic, art-filled room famously serves as a backdrop for visiting music royalty and filmmakers who come to hand-select pristine Adriatic seafood directly from a raw table display.”
Pai Northern Thai Kitchen, 2335 Yonge Street: “The ultimate detour for high-profile travellers looking to experience the raw culinary heartbeat of the city away from formal fine dining,” he explains. “This high-octane, incredibly popular spot is a cultural phenomenon celebrated for its fiercely authentic Northern Thai street food.”
Drink

Bar Pompette, 607 College Street: “A crown jewel of the city’s nightlife, ranked as the #2 bar in the country on Canada’s 50 Best Bars list and #8 in all of North America,” Hollywood explains. “This Little Italy sanctuary blends the effortless charm of a Parisian café with a globally elite, ultra-innovative cocktail program, making it a mandatory stop for high-profile cocktail connoisseurs.”
Bar Raval, 505 College Street: “A globally ranked cocktail destination housed inside a jaw-dropping, Gaudí-inspired mahogany masterpiece,” he says. “It provides a sensory late-night atmosphere and world-class Spanish tapas, making it the definitive stop for an upscale nightcap.”
Play

Private Shopping at Holt Renfrew: “For the ultimate high-end retail experience, I coordinate with the flagship Holt Renfrew on Bloor Street for completely private, after-hours shopping,” he explains. “They will close down specific designer boutiques or entire floors, draw the blinds, and provide dedicated personal stylists so stars can browse the latest luxury collections in total peace and comfort.”
Private Yacht Charters: “To experience the city without the crowds, a concierge can arrange a luxury motor yacht charter out of the Harbourfront,” he adds. “Cruising through the quiet lagoons of the Toronto Islands offers an ultra-private oasis complete with a dedicated captain, hostesses, and premium champagne service, allowing high-profile guests to relax against the backdrop of the iconic skyline in total seclusion.”














