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The Place Bonaventure is widely recognized as one of the most important buildings constructed in Canada in the 1960s, though that’s not to say it’s universally loved. It’s a regular contender for the title of Montreal’s ugliest building. For the student of architecture, however, whether armchair or otherwise, it’s worth a visit to see an outstanding example of brutalist architecture. Architect Raymond Affleck’s vision was to turn the city inside-out in a building appropriate for its location in a cold climate. The Place Bonaventure was designed to include a conference center, hotel, and several floors of retail space, all along internal streets while the building presents a foreboding exterior of ribbed concrete (echoing the design of the seminal Architecture School at Yale University by Paul Rudolph) to the street. The entire complex included 3.1 million square feet of floor space, making it the largest building in the world when it was completed (in 1967). Much of the retail space was converted to offices in later renovations, though the conference center and the hotel (now the Hôtel Bonaventure Montréal) remain. The photo here was taken inside the hotel—a walk around their common spaces will give you a taste of Affleck’s vision for a new urban architecture.

In the heart of Whistler Village, Sundial Boutique Hotel is about as central as you can get: Three gondolas to Whistler and Blackcomb mountains sit right outside your door, and the area’s restaurants, shopping, and nightlife are only steps away. With just 49 suites, it’s one of the smaller properties in town, but the rooms themselves are generously sized and include full kitchens, dining and sitting areas, and gas fireplaces. For those who don’t want to splurge on a suite with a private outdoor whirlpool, you’ll still have access to Whistler’s only rooftop hot tub. And while the property doesn’t have its own swimming pool, guests are free to use the one at the lodge next door from May through October.

While Campobello Island is located in the Canadian province of New Brunswick, the only access to it by car is by crossing the International Bridge from Lubec, Maine. The 2,800-acre park honoring President Franklin D. Roosevelt covers most of the island’s southern end. The Visitor’s Centre and the Roosevelt Cottage are about a mile from the bridge. Begin there, and register for Tea with Eleanor, an engaging one-hour program during which park interpreters share stories about the former First Lady’s visits to the island over tea and cookies. After touring the 34-room, memento-filled, red-shingled cottage and the exhibits at the Visitor Centre, pick up park maps and explore the carriage roads, picnic areas, beaches, woodlands, lighthouse, hiking trails, and scenic viewpoints.

This rickety old five-storey loft building downtown became an enclave for art galleries a couple of decades ago because the rents were affordable and the location was central. Management has since embraced its status as Montreal’s small-gallery and artist-run centre headquarters, and spruced the building up a bit, encouraged by the enthusiastic foot-traffic the galleries bring. Some mainstays absolutely not to be missed on your trip there include Pierre-François Ouellette Art Contemporain (pictured), where you might catch art by Kent Monkman, Maskull Lasserre or Karilee Fuglem; Circa, an exciting space in constant development these days, dedicated to sculptural works; and Galerie Joyce Yahouda, an effervescent space where you can see work by local artists including Céline B. La Terreur, François Morelli or David Elliott.

Among the city’s coolest art spaces, Fonderie Darling is a giant – and I mean GIANT – industrial space-turned-contemporary art gallery. It’s a shining example of the type of architecture that existed in the area before the rapid gentrification. Divided into two halves, the space generally hosts one monumental work or series of works in the cavernous main area, and a smaller, more human-scaled exhibition in the second half. Fonderie Darling is also home to a dozen or so artist studios for artists-in-residence from around the world, which one can occasionally visit. Make an evening of it and reserve a table at the Fonderie’s restaurant, Le serpent, one of the hottest addresses in town.

On Jean-Talon near Parc Avenue in the rapidly gentrifying neighborhood between Mile End and Park Ex known as Mile Ex, Bar Le Ritz PDB is a large open space with a few tables by the big front windows (always open in summer afternoons so that the fun spills out into the street) and a warm, relaxed atmosphere. It’s better known as a show-bar than a hangout bar, though that is slowly changing with expanded opening hours and a wider range of drink options. Like most Montreal music clubs, anyone can reserve a spot to play here; but the average night tends to lean towards indie rock, post-punk, alternative pop sounds.

When it isn’t occupied by the Grands Ballets Canadiens or Opéra de Montréal, this largest concert hall in Montreal’s Place des Arts cultural complex has been known to host big musical names, including Maria Callas, Bob Dylan, Radiohead, Luciano Pavarotti and Ella Fitzgerald. The sound system is the utmost in refinement, and, combined with the cushy seats and hushed atmosphere, it makes for a sophisticated listening experience indeed. Half the fun is the opportunity to wander through the impressive 1960s building, punctuated by salons and bars for that ubiquitous intermission gin & tonic. Go ahead of time and reserve a table at one of the famous glassed-in restaurants on the Quartier des Spectacles, Brasserie T! or F Bar.

Walking through the first set of double doors offered warmth from the cold and snow outside. Walking through the second set, we were smacked in the face by the glorious smells coming from the wood fired ovens and the pizzas baking within.

Brewhouse brews 5 of their own beers and has a menu ranging from Matzo Ball Soup to 4 different types of Poutine.

Wait for a table upstairs or order off the full menu at the bar or by the fire in their cozy lounge.

“She’s an original yet timeless Québec fashion designer—a rare combination. Marie Saint Pierre is known for using unusual fabrics with soft colors as well as black and white. Her designs feel really classic. I stop in when I need something chic and comfortable,” says Nathalie Bondil, head curator at the Montreal Museum of Fine Arts.

Whistler Blackcomb doesn’t do anything small, so it was no surprise that Whistler Bike Park quickly emerged as the global go-to, lift-access, downhill-biking destination. The park even has its own massive festival, Crankworx, a 10-day rock-hopping frenzy every August. Walking among the armored throngs rolling their studded-tired bikes toward the lifts, you could forget that it snows here at all. Any thoughts of summer being the off-season have vanished. You don’t have to be a millennial—though it helps—to get dirty here; there are more than enough green and blue runs to provide a serious rush for youngsters and boomers. Sign up for the park’s outdoor clinics for critical insights into your technique.

The Gastown neighborhood dates back to the Victorian era when “Gassy Jack” Deighton opened a saloon in a burgeoning sawmilling settlement. Now its grand heritage buildings—in Romanesque, Edwardian and Victorian Italianate styles—and brick-paved streets are home to art galleries, design shops and stylish eateries. Don’t miss the statue of the storied tavern owner in Maple Tree Square and Water Street’s famous steam clock, built in 1977, which sounds off every 15 minutes.

At 185 acres, the Montréal Botanical Garden is less than a third the size of Mount Royal Park, but it manages to fit a remarkable collection of some 22,000 plant species and cultivars into that space, organized into 20 thematic gardens and including 10 exhibition greenhouses (ideal if you are looking for some tropical warmth in the depth of a Montréal winter). Everyone will have his or her own favorites when it comes to the different spaces—Alpine, Chinese, Japanese—but the First Nations garden stands out. Wandering alongside its pond and following its forested trails, you’ll feel like you are far from the city and instead in the northern reaches of the province of Québec—at least until you catch sight of the swoop of the nearby Olympic Tower, with its distinct incline. You can continue the naturalist itinerary at the Biodome, also nearby, where five different ecosystems of North America are re-created with flora and fauna—auks, lynx, penguins, and more.

Perched on Laurier Boulevard in one of Quebec City’s main commercial districts, the Hôtel Plaza Québec draws its fair share of business travelers. But it’s an even better choice for families thanks to its indoor swimming pool and hot tub set within a ground-level tropical garden; there are also two play rooms, a movie room, and regularly scheduled activities for the young set. While standard rooms are cozy enough for solo travlers, larger accommodations range from suites with kitchenettes to loft-apartments that can sleep as many as 13 people. Drop your bags, then take advantage of the hotel’s proximity to Old Town’s most popular attractions (about five miles away), as well as the impressive Aquarium du Quebec and the Parc de la Plage-Jacques-Cartier, with its riverside beaches and walking trails.

In the heart of Old Québec’s Upper Town, Hotel Manoir Victoria blends 19th-century grace with an updated urban-chic vibe. A recently completed $8 million makeover of the 1830 property’s accommodations added a calming palette of ebony, gray, and cream and amenities like electric fireplaces and living areas, as well as iPhone chargers, rain showers, and pod coffee makers. Guests have no shortage of diverting destinations to choose from, including a spa, indoor saltwater pool, and fitness center. The hotel’s gourmet restaurant, however, usually beats out the competition, earning high praise for its thoughtful Nordic-inspired Québecois cuisine using seasonal, locally sourced, and foraged ingredients in dishes such as carpaccio of elderberry-marinated arctic char with cattail heart and milkweed pod.

Le Petit Hotel is housed in a former leather merchant’s building that dates back to 1867 and boasts original stonework arches and pillars at its entrance. Truly a “petit” hotel, its 28 rooms are spread across four floors and divided into S, M, L, and XL. Although it’s small, the hotel packs a stylish punch, mixing century-old exposed brickwork and stone with funky hardwood floors and modern-day luxuries—from free Wi-Fi and iPod docks to platform beds and multi-jet massage showers. In the guest rooms, splashes of bold, sunny orange and black accents create a contrast to the fresh white walls. Situated in the heart of Montreal’s fashionable Old Port area, guests are just steps from much of the city’s best shopping, dining, and art.