I arrived in Toronto this fall, as many do each year, intending to spend most of my stay huddled inside a frigid movie theater. After all, September in the Canadian cultural hub is home to the beloved Toronto International Film Festival, which beckons celebrities, film buffs, and media types like myself to argue about the latest and greatest in cinema (and, ideally, predict the next Oscar winners). My first time at the festival was in 2023, which also marked my first time in Toronto. At that point, the idea of venturing far outside a screening room felt equally overwhelming and unlikely. But as soon as I spent more than five minutes turning in circles around the streets outside my hotel, I grew enchanted with the food, the weather, the architecture, and the history of the city—and found myself slipping away between films as often as possible.Along the way, I enlisted a guide from the Toronto Society of Architects to point out the city’s fascinating blend of old-school British style and boundary-pushing modern construction. With his help—and some exploring of my own—I discovered spots I was eager to revisit on my subsequent trips up north. Since then, I’ve returned to Toronto for multiple visits, and I find myself falling in love more and more with each stay. The below recommendations offer a hand-picked entry point for the Ontario beacon—particularly if you only have a few days to spare. Whether you’re planning a trip for TIFF next year or keen to avoid the lanyard-adorned crowds, here are a few worthy gems for the journey.What to SeeKensington MarketNick Wons/Courtesy of Destination TorontoOne of the most popular neighborhoods in downtown Toronto, Kensington has a eclectic appeal that residents and visitors have enjoyed for decades, as numerous immigrant communities have moved in and through the charming storefronts, each leaving a permanent footprint on the makeup and attitude of the area. Set aside a few hours to meander amongst the wall murals and aging Victorian homes while stopping by specialty food purveyors, cafés and restaurants, arts spaces, and clothing boutiques. Vintage hounds, in particular, will find much to discover (and adore) from Courage My Love, Flamingo Vintage, funky costume mainstay Exile, and numerous other thrifty depots. Get caffeinated at Moonbeam Coffee, Jimmy’s Coffee, or Fika before you begin your stroll. Once you get hungry, stop for steamed dumplings at Mother’s Dumplings or some cheese and charcuterie at Cheese Magic.The Distillery DistrictCourtesy of Destination TorontoOfficially opened in 2003, the Distillery District is a pedestrian-only zone southeast of downtown Toronto, and the home of numerous red-brick Victorian buildings that housed the former Gooderham & Worts Distillery, once the largest distillery in the British Empire. Eventually abandoned in the 1990s, the area’s owners decided to reinvent the neighborhood as a stronghold for arts and culture while preserving the historic look and feel. Today, visitors can explore cobblestoned streets lined with bars and restaurants, shops and offices, art galleries, and theaters. Sip a coffee from Arvo Coffee before a classic combo of beer, burgers, and poutine from Mill St. Brew Pub, then peruse art at your leisure: Thompson Landry Gallery, Arta Gallery, and Corkin Gallery are all apparent local favorites.Royal Ontario MuseumWalter Bibikow/Courtesy of Destination TorontoThe Royal Ontario Museum’s jagged crystal-inspired entrance, fused to the classic brick-and-stone exterior, is a love-it-or-hate-it sight for many Torontonians, but there’s no question that what awaits you inside is a wonder to behold. The ROM is Canada’s largest museum, and the sheer number of treasures on offer is almost overwhelming, mixing tiny artifacts of ancient civilizations with jaw-dropping dinosaur skeletons. (A delight for my husband and me, especially when our guide presented us with a dino tooth to balance on our palms.) Daily tours are free upon admission, and I highly recommend joining one—unless you’d prefer to get lost amongst the suits of armor and mummy sarcophagi, which, truth be told, sounds just as fun.Everlane The Buttersmooth Oversized BlazerCredit: EverlaneLoewe Anagram Appliquéd High-Rise Wide-Leg JeansCredit: Net-A-PorterBared Footwear Maleo Black Leather LoafersCredit: Bared FootwearWhere to EatRasaCourtesy of RasaA cozy-meets-industrial spot with exposed materials and an outdoor patio nestled in Harbord Village, Rasa serves sharable global-fusion bites and entrées for a leisurely but delicious course-by-course delight. Sample the chopped salad with chickpeas, grilled octopus with green mole, and the lamb dumplings with vindaloo, but make sure not to stuff yourself ahead of dessert: The sticky bun with cream cheese anglaise and candied bacon was a melt-in-your-mouth delicacy, one I’m still dreaming about months later.Piano PianoCourtesy of Piano PianoEver considered slicing your pizza not with a roller but a pair of personal scissors? At Piano Piano, that’s the (Instagram-ready) norm. A multi-location staple in Toronto, Piano Piano serves sleek-but-classic Italian fare for lunch and dinner in four different spots throughout the city, with each interior dreamed up by a Toronto-based designer. The name, which comes from the Italian phrase piano piano va lontano, meaning “slowly slowly we go further,” matches the relax-and-enjoy-yourself attitude of the restaurant itself. Pizza is a clear hero here—I particularly enjoyed The People’s Champ, a prosciutto-and-arugula-adorned pie—but pasta, meat, and fish are equally celebrated. If you’re dining in a group, be sure to consider the Dinner for Two or Family options, which allow you to taste the “greatest hits” for a fixed price.CanoeHector Vasquez/Courtesy of CanoeThe ideal spot for an upscale date night with sweeping views of the Toronto skyline, Canoe rests on the 54th floor of the TD Centre, allowing visitors a picturesque look at the CN Tower and surrounding city landmarks. But the looks aren’t the only draw to one of Canada’s most acclaimed restaurants. Canoe serves so-called “haute Canadiana” cuisine, presenting elegant spins on timeless national dishes. The menu is seasonal, adapting to whatever’s fresh and flavorful—fish, mushrooms, meats, and vegetables sourced from throughout Canada—but expect an always-genius raw bar alongside a rotating tasting menu. With a well-stocked wine list and plenty of hand-crafted cocktails with which to whet your appetite, Canoe does everything it can to match the hype.Khaite Women's Milo Cashmere Sweater - Black - Size XSCredit: KhaiteSilk Laundry Long Bias Cut SkirtCredit: Silk LaundryM. Gemi The Tina BootsCredit: M. GemiWhere to DrinkMother Cocktail BarCourtesy of Mother's Cocktail BarOne of the most celebrated cocktail bars in Toronto—if not all of Canada—Mother uses its on-site fermentation room to shake up unique (and beautiful to behold) delicacies. Unexpected ingredients like horseradish, black garlic, caramelized yogurt, candy cap mushrooms, and bee pollen intermingle with indulgent spirits and liqueurs to make a visit to Mother feel like its own multi-course meal. The excellent bar menu means you can stay for a real multi-course meal, too. Start with sourdough bread with red miso butter, then pair udon noodles or jerk chicken karaage with your drink of choice. Or craft your own cocktail with Mother’s Symbiosis experience, in which you select a base spirit and a seasonal ingredient, then inform the bartender of your palate, and they’ll whip up something to your liking. Those who prefer a non-alcoholic option won’t feel forgotten, either: Bee pollen lemonade and seasonal kombucha give the same nuanced flavor without the hangover.Cry Baby GalleryRick O’Brien/Courtesy of Cry Baby GalleryA not-to-be-missed culture-and-cocktails synthesis, Cry Baby Gallery in Toronto’s Little Portugal is indeed an art gallery, featuring exhibitions that “[bridge] the gap between fine art and street art.” But those in search of refreshments can find a New York-style speakeasy hidden in the building, where the cocktails are a work of art unto themselves. The bar is first-come, first-serve, so head to the dim, neon-lit industrial space in the rear of the gallery to snag a chair (and a spicy margarita) before the crowd shuffles in.KŌSTCourtesy of KŌSTKŌST sits atop the 44th floor of the new BISHA, a Luxury Collection Hotel, in downtown Toronto. Inspired by the beachy vibes and flavors of the California coastline, KŌST serves breakfast, lunch, and dinner (plus snacks and cocktails) seven days a week, as well as an everyday brunch. (I still dream about the tropical pancakes—drizzled in an agave maple syrup and pineapple mango salsa—weeks after tasting them.) But it’s a particularly perfect spot to watch the sunset, cocktail in hand. Airy and filled with natural light, offering both indoor and outdoor seating with panoramic views of the downtown skyline, KŌST boasts a wide range of delicious drinks. Don’t sleep on the Baja-rita.L'Agence Sayla Silk GownCredit: L'AgenceCult Gaia Caldera ClutchCredit: Cult GaiaAstrid & Miyu Molten Large Hoops in GoldCredit: Astrid & MiyuWhere to StayW TorontoBrandon Barré Photography/Courtesy of W TorontoColorful and contemporary with a playful, nightlife-inspired aesthetic, W Toronto enjoys a prime spot in the ritzy neighborhood of Yorkville, where brands such as Chanel and Christian Dior have planted brick-and-mortar stores in the buzzy shopping and dining scene. (For a multi-brand luxury shopping experience in the area, I recommend The Webster.) Inside you’ll find the W Living Room, the lobby-meets-restaurant-meets-coffeehouse-meets-club, where fellow guests can convene for afternoon tea, cocktails, delicious food, and live events. If you’re into music (or podcasting), book a session at the W Sound Suite, where you’ll find all the equipment you need to lay down a track (or just blast your favorite albums). Jewel-toned suites featuring trendy geometric designs make W Toronto’s accommodations feel plush yet fashionable.Shangri-La TorontoVRX Studios/Courtesy of Shangri-La TorontoClassic elegance defines the Shangri-La Toronto, a five-star beacon in the midst of the action downtown. Guest suites merge the hotel brand’s signature East Asian-influenced décor with indulgent amenities: skyline views, heated marble floors, deep-soaking tubs, and in-room iPads to get the temperature and lighting just right. A 20-meter lap pool rests beneath a glass roof in the 9,000-square-foot health and fitness area, where you’ll find top-of-the-line gym equipment alongside a sauna and steam room. (But carve out additional time for the Miraj Hammam Spa, an award-winning wellness space where you can enjoy personalized massages, clean-beauty facials, and full-body contouring.) Catch a film in the 42-seat movie screening room, and book a reservation at the ground-floor Italian restaurant, bosk. Each fall, the accomplished bartenders develop a new speciality cocktail menu with ingredients inspired by cinema classics and the year’s favorite fest films. Last year, I tried (and adored) “The Sound of Music,” a fizzy confection served in a Erlenmeyer flask-like container atop a mound of moss and fake flowers.BISHA, a Luxury Collection HotelCourtesy of BISHA, a Luxury Collection HotelNewly opened this past spring, BISHA, a Luxury Collection Hotel, is in the prime location for TIFF movie-goers who prefer a stylish, rock-star-worthy stay. (Lenny Kravitz’s Kravitz Design is responsible for a smattering of the BISHA suites.) Situated right off of King Street, where much of the TIFF action takes place, the boutique luxury property features bold, contemporary furnishings in each of its 96 rooms, as well as in its dramatic lobby and dining offerings, which include chef Akira Back’s namesake restaurant and the rooftop oasis KŌST. During my stay, I spotted multiple A-listers making their way to and from BISHA, including Frankenstein star Jacob Elordi...but, to be honest, it might have been the heated floors in the bathroom that I appreciated most.Elwood Clothing Oversized Core CrewneckCredit: Elwood ClothingElwood Clothing Core SweatpantCredit: Elwood ClothingStrathberry Melody ToteCredit: StrathberryBeauty PicksDIME Hyaluronic Acid SerumCredit: DimeHydration is an absolute essential when traveling, and I’ve fallen in love with the simplicity and effectiveness of Dime’s Hyaluronic Acid Serum, which makes my skin feel soothed and soft after one tiny dropper of product. The little bottle is easy to stash away in your carry-on, meaning you can bring it out whenever your skin needs a mid-flight boost.Charlotte Tilbury Hollywood Flawless FilterCredit: Charlotte TilburyMy new holy-grail product, the Charlotte Tilbury Hollywood Flawless Filter gives me an effortless glow while evening my skin tone and blotting any blemishes. Particularly when I’m sprinting between stops in a packed itinerary, I want to know my skin tint is going to last amongst the sweat, smog, and (occasional film-induced) tears. With this little tube, I never have to worry.Glamnetic Press-On NailsCredit: GlamneticWhen I’m heading to a movie premiere, I want to know my nails look red-carpet ready—but I don’t want to fit a salon appointment into my schedule. I’ve tested a number of press-on nails to alleviate that problem, and my favorite brand by far is Glamnetic. I can wear these nails for up to two weeks, and they look gorgeous the whole time.Advertisement - Continue Reading Below