Lately, more and more Americans are looking north, and Toronto is the perfect reminder that crossing the border can feel like a true escape, with all the culture, food, and charm you could want, just a quick flight away. The city is clean and cosmopolitan, like New York’s cooler cousin, who reads poetry, wears Sid Neigum, and always knows the best wine bar before it opens. It’s got all the ingredients anyone could want in an urban escape: excellent food, a global wine list, culture on every corner, a live music scene that punches way above its weight, and charming, walkable neighborhoods that keep delivering surprises.
Whether you’re craving a summer rooftop drink or a museum day in the middle of a rainy spring, Toronto works in every season. My go-to? A two-day reset that includes natural wine, local art, a luxurious hotel, and a night out for fondue and unparalleled cocktails.
Let’s start with where I landed: the Shangri-La Toronto, a sleek, tranquil five-star sanctuary in the heart of downtown. The rooms are a dream, featuring plush king beds, heated bathroom floors, and a soaking tub with a view of the CN Tower that became my unofficial morning ritual. A Fazioli piano with Joni Mitchell lyrics engraved inside its lid anchors the lobby lounge, where you can sip oolong and listen to live music, or kick off happy hour with caviar and Champagne.
The real win? Check out bosk, the hotel’s signature restaurant, which serves Northern Italian cuisine, using fresh, seasonal Canadian ingredients. If you’re not up for a full meal, the Lobby Lounge serves a killer afternoon tea and late-night snacks. There’s also a serene spa and wellness floor featuring a 20-meter indoor pool, hammam, infrared sauna, and a luxurious treatment menu. If you’re in the mood for something more cinematic, the hotel can even arrange a helicopter to Niagara for a day of wine tasting in Ontario’s most prestigious wine region.
Be sure to visit the Art Gallery of Ontario (AGO), a stunning redesign by Frank Gehry that’s as much about the architecture as the art. The Canadian contemporary wing is a highlight, and its special exhibitions often feel fresh and globally relevant, featuring topics such as hip-hop photography, Indigenous futurism, and feminist painters. Don’t miss the spiral staircase or the gift shop, which rivals MoMA’s in both curation and design.
A quick walk from AGO will lead you to Grape Witches, a funky, feminist-forward natural wine bar that feels like it could exist in East Nashville or Silver Lake, but with a distinctly Toronto vibe. Think low-intervention Canadian wines, retro glassware, briny snacks, and staff that’ll talk you into trying a blackcurrant cider that tastes like nothing else in your glass all year.
Grab dinner at Bar Piquette, where I revisited my love of fondue—cheese, bread, white wine, repeat. It’s intimate and candlelit and feels like a scene from a French film, with servers who actually care about what you’re drinking. The menu includes hard-to-find wines expertly paired with European-inspired small plates. The kind of place that’s made to linger.
To cap off the evening, go full sensory with cocktails at BarChef, a moody, modernist lounge founded in 2008 by Frankie Solarik, a pioneer in modernist mixology. Solarik’s approach involves crafting cocktails that engage all senses—taste, smell, sight, and touch. Each drink is meticulously prepared using house-made infusions, bitters, and syrups, often incorporating elements such as dry ice, edible gels, and aromatic garnishes to enhance the overall experience. My drink arrived with a hint of cedar smoke, a chilled ceramic bowl, and a shot of something herbaceous that reset my palate in the best way. Pro move: Sit at the bar and let them surprise you.
Toronto’s neighborhoods are tailor-made for wandering:
- Queen Street West is your go-to for indie boutiques and art galleries.
- Kensington Market offers a diverse range of vintage finds, secondhand records, and international snacks.
- Yorkville is an upscale neighborhood with designer stores, cafes, and galleries nestled into restored Victorian rowhouses.
- If the weather’s right, rent a bike and head to Toronto Islands for skyline views and an afternoon picnic.
For a rooftop view, nothing beats the CN Tower. It offers the most iconic aerial view (and it’s worth doing at least once), but for a stylish rooftop drink with a skyline vibe, head to Harriet’s Rooftop at 1 Hotel Toronto for a pre-sunset drink. It’s one of the best skyline views in the city—stylish, with a DJ and craft cocktails that rival anything in Brooklyn or Barcelona. Bonus points for the eco-forward vibe and rooftop, which makes it feel like a summer escape even in the shoulder season.
And the music scene? Always at the top of my list. On this trip, I lucked out with Phantogram at Danforth Music Hall, but you’ll find someone interesting playing almost every night—at Massey Hall, Horseshoe Tavern, or a jazz basement in the Annex. Toronto lives and breathes music, and the audiences are in it for the right reasons.
As I stood by my hotel room window the next morning—espresso in hand, CN Tower framed in glass—I realized: Toronto is one of those rare cities that doesn’t scream for your attention. It just quietly offers you everything.
TORONTO TRAVEL TIPS
Stay: Shangri-La Toronto – Splurge on a room with a view. Don’t skip the spa.
Drink: Grape Witches for natural wine; BarChef for cocktail theatre.
See: Art Gallery of Ontario; Frank Gehry meets modern Canadian genius.
Eat: Bar Piquette for fondue and seasonal fare; Bosk for a luxe dinner.
Shop: Queen West, Kensington Market, and Yorkville.
Do: Helicopter to Niagara, explore the islands, or hit a live show.
