When you tell people you grew up in Montreal and moved away (in my case to Toronto nine years ago), the common reaction is “why would you leave??” Montreal, after all, is a charming European-feeling city of infinite delights. A small town vibe in a big city package, where love of art, food, drink and nightlife permeates every corner. It’s a place where your urban teenage years and rollicking early twenties fly by in a blur of summer fireworks, downtown bars, and dizzy dance floors, memories lodged in your psyche like wads of Bubblicious stuck to Seattle’s Gum Wall.
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But it’s also a city where, if you spend a few decades, you’re likely to also collect some battle wounds. Quebec’s slogan is “Je Me Souviens,” meaning “I remember,” and despite years of joy, freedom and growth, and Montreal’s elysian reputation, there were some moments I’d rather forget.
That’s why, after almost 10 years of being away and at least twice as many visits to ailing parents that felt like, well, work, I resolved to return with my fiancé Dustin and toddler son Oslo in tow and just enjoy it. To reclaim some of the magic that was lost in the years since I left, my mission started in Old Montreal, which was the last place I lived before my great escape. A tourist mecca, it’s busy, sure, but also inarguably oozing with charm. I booked as few obligations as possible in an effort to slow down. Meander. Eat. Sit. Sip. Sleep. Repeat. It was, in a word, divine. I spent a few days in my old city with my new family, the one I created for myself, and visited with the ones I left behind. A sweet birthday brunch with old friends, a visit to my dad, and a beautiful dinner all punctuated the mostly itinerary-free sojourn.
After a few nights of delightful tourist leisure, I left my old hometown behind and returned to Toronto with new memories instead of anxiety about the old. You can’t ever truly go home again, but you can find a welcoming spot to rest your head before returning to your new one. Here are some of my Montreal faves.
The superior neighbourhood: Old Montreal
As mentioned, the decision to stay in Old Montreal was not a random one. It was the last place I lived in the city before relocating to Toronto and while I relished living in a classic converted loft in the heart of the neighbourhood, I longed to experience it like a visitor. And it didn’t disappoint (except for when my toddler would break loose and from my grip and run like an escaped prisoner into throngs of people). From the charm of the cobblestone streets stunning European architecture and the stunning views to the array of restaurants, cafes and cute shops (all within walking distance), it really can’t be beat.
Pro tip: Factor the cost into your travel budget and park your car in a lot or do valet at your hotel. The stress of trying to find and keep street parking simply isn’t worth it.
The chic hotel: William Gray
Where to begin on this magical property? From the outside, the Hotel William Gray looks like an 1800s cottage meets a modern hotel (in fact, the property is comprised of two 18th-century stone homes topped with a sleek glass tower) and inside, the amenities are unparalleled. There are countless tricked out lounge areas for chatting, drinking or getting some work in. There’s a sleek pool in the summer and an outdoor patio with fireplaces and comfy Muskoka chairs. There’s a rooftop patio with insane unobstructed views of the waterfront. There’s an onsite restaurant, Maggie Oakes, with sleek wood booths and one of the best pain au chocolat I’ve ever had. Plus, the rooms themselves are superior in every way, from the deliciously cozy king-size beds to the Le Labo toiletries. (Did Dustin fill his Dopp kit with Santal 33 minis? I’ll never tell.)
Pro tip: Make time for a gorgeous glass of Prosecco at Maggie Oakes before heading to your dinner plans. Slide into one of the metallic barstools at the pristine marble bar — santé!
The iconic coffee shop: Café Olimpico
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Ah, Café Olimpico. The OG location in Montreal’s Mile End where I once lived is such an institution that you almost invite the anxiety that waiting in its intimidating line causes. Will I place my coffee order quickly and succinctly enough? Will the slightly stern but secretly sweet barista behind the counter even notice me? If I come here daily for two years, will I finally be treated like a regular? The Old Port outpost, located conveniently within the William Gray hotel, is smaller (and ridiculously cute) but still offers the same superior espresso Olimpico is known for. They get extremely busy but the line moves quickly and the staff at this location is very friendly.
Pro tip: Get the lemon cake. Don’t ask questions.
Check out more of the best hotspots in our Montreal travel guide here:
The ideal spot for extended stays: Warwick Le Crystal
If space and comfort are what you’re after, Warwick Le Crystal (formerly Hotel Le Crystal, which was the city’s only independently owned five-star hotel) is a must-visit. Recently acquired by Warwick Hotels & Resorts, this downtown location can’t be beat and its oversized rooms are perfect for longer stays or family vacations. Every single suite in the hotel features a kitchenette and king-sized bed, and fun fact: many of the suites have attached balconies. One particularly stunning penthouse suite features not one but two oversized balconies (one on either side of the living area), while another suite boasts a terrace that is larger than most one-bedroom apartments in Toronto. Everything’s bigger in Texas Montreal, it turns out.
The lush spa: Guerlain Spa at Four Seasons Montreal
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Skin in need of a boost before we head into cooler temperatures? Get yourself to the Guerlain Spa located in Four Seasons Montreal, stat. Offering luxury treatments like facials, massages and body treatments, you’ll leave feeling rejuvenated and ready to take on the long, blistering winter season. (Er, as ready as you can be.)
The cute cocktail bar: Knox Taverne
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Fancy a cocktail? Knox Taverne will hit the spot. Serving up creative cocktails and an excellent wine list (not to mention delicious sharable plates, if you want to nibble) in a cozy setting, you won’t want to leave this intimate Pointe St. Charles hangout spot. Come for the sips and bites; stay for the décor (gorgeous herringbone floors, plants and string lights galore).
The can’t-miss restaurant: Damas
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Serving up authentic Syrian flavours in a lush setting (think jewel-toned lanterns and dark polished wood), Damas offers an unforgettable dining experience. It’s no wonder the restaurant was named one of the best places to eat in Canada.
The quintessential Old Port hotel: Auberge du Vieux-Port
With waterfront views of the St. Lawrence river, exposed brick walls and original wooden floors that creak just the right amount, the Auberge du Vieux-Port offers the most authentic Euro-inspired experience. The charm of this 19th century property, comprised of two converted warehouses, is unbeatable but its hotel amenities are decidedly modern and luxe. Think: a wrought-iron bed straight out of Jane Eyre, but with a cloud-like king-size mattress. Did I mention the bathroom is spacious and the soaker tub is big enough for two? (In my case, me and my toddler — and his bath toys.) For the ultimate night in, grab a cheeky cocktail in their wildly cozy lobby lounge, complete with roaring fireplace, and then get Italian takeout from Jacopo just around the corner to keep the chill vibes going. The mushroom risotto is unmatched.
With files from Souzan Michael Galway
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