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Castle Ho’s motto, the owner of lovely boutique 1861, is quite simple. “Women who love being women and dressing the part.” Such is the premise of her work, and it definitely transposes into her boutique. The store is decorated in what seems to be a vintage fashionista’s dream: airy space, high ceilings,Vvictorian inspiration, and soft eggshell, champagne and pastel pink hues everywhere. No boys allowed! The multi-brand store focuses on feminine, timeless pieces first and foremost, and incorporates up-and-coming designers into the mix, like UK-based Emily and Finn and Torontonians Pink Martini, along with Montrealers lines Coccolily and Arti Gogna. Don’t be fooled by the perfect, fairy-tale decor; the prices are more than fair and very few things are over $100 in the store. Guilt-free, stylish shopping? I like.

The Evergreen Brick Works, a reclaimed quarry in the lush Don Valley, is a showcase for sustainable and green living, as well as for urban design. A community has been established in this once-derelict industrial site and former landfill. Toronto’s largest farmers’ market sets up shop on Saturdays, and spotlights food from all over the province. On Sunday, the market shifts its attention to crafts. A full schedule of activities and diversions make this a perfect weekend escape: There’s a children’s garden (with weekly programming), bike trails and rentals, and a hike that leads to a rewarding view of the city’s skyline.

IndexG B&B was an art gallery before the owners renovated the second floor into a four-bedroom bed and breakfast. Housed on a sleepier stretch of Gladstone Avenue but close to the action of both the West Queen West and Parkdale neighborhoods, this family-run B&B offers affordable rooms and minimal amenities. Art is displayed throughout the hotel, and it is all available for purchase. With much to do in the area, this is a well-located hub from which to discover the best of Toronto.

Among the neighborhood’s art-minded hotels, the Gladstone is the most interactive, with shows, classes, and ongoing events. The 37 rooms, all designed by local artists, have breathed new life into the 128-year-old icon, which filmmaker Christina Zeidler took over in 2003 and revitalized in 2005. The Victorian landmark, named for its avenue (in turn named after four-time Canadian Prime Minister William Gladstone), has been a gathering spot for over a century. And it was home to legendary Toronto characters like cowboy Hank Young, who became a fixture at the hotel as a country singer in 1961 and manned the hand-operated elevator from 2005 to 2009, and Peter Styles, former host of Karaoke Night, with applause sign in hand. The legend of Hank lives on in a framed photo in the stairwell en route to the second floor.

The Gladstone continues to push the boundaries of community and culture with creative events like its educational workshop series, Get School’d, and its annual alternative design event, Come Up to My Room (CUTMR), which runs alongside the city’s Interior Design Show. Begin your stay in this architectural gem with a drink at the Café or Melody Bar (that is, if you’re not first thrust into Fameless Karaoke Night).

Since it was built back in 1976, the CN Tower has topped the must-visit list of most Toronto tourists. Until recently, a visit was pretty standard; hop in elevator, shoot up to the observation deck, and ogle the city from a hawk’s vantage point. While this was certainly fine and enjoyable, the since-developed EdgeWalk experience has ramped up the Tower’s bucket-list potential. Thrill-seekers can now do a hands-free, breezy circumnavigation of the tower’s roof, up at 1,168 feet. And, yes, they do perform sky-high weddings complete with elasticized rings and special attire for the big day.

Suddenly, grub that is both Chinese and Jamaican is a thing. Chef Craig Wong, third generation Chinese-Jamaican himself, has taken over a Dundas West space and done quite the number on the local dining scene, turning out a cuisine of his own that manages to encapsulate all that is Toronto. Pick from eats like the Jamaican patty double down — chef’s take on the famed KFC number — and the dirty fried rice with red sausage and peas. For a small group, go with the so-called Whole Shebang and test out Wong’s take on jerk chicken. Dinner can be reserved, but if you’s aiming for brunch, be there when the place opens and tuck into the Hong Kong-style waffles and the luscious maple butter French toast.

Discounted Lindt Swiss chocolates—really, what is not to love about this? You’ll find a wider-than-usual Lindt range here, which means flavors you don’t often see in the shops, from pistachio to sea salt and even Irish cream.

Usually, when you travel, it’s to experience a different side of yourself. The more adventurous side, the slightly less scheduled side, the sleep-in-without-guilt side. And when you stay at the Drake Hotel in Toronto, you can’t help but feel like your cooler side is making a much-needed appearance. The recently renovated property on Queen Street West features the kind of interior design that radiates style whether it’s in the kaleidoscopic lobby, the next door theater, or in two wings of suites. That’s because the hotel commissioned artists to showcase their work on plenty of open surfaces — from a black-and-white squiggle accent wall in guest rooms to personality-driven drawings in the elevator — and the results make for surroundings that are the material equivalent of black sunglasses. Paired with of-the-moment details like pink terrazzo showers and wraparound midcentury sofas, and the Drake Hotel is meant to cultivate a see-and-be-seen vibe.

But that’s not to say that the hotel sacrifices comfort for being camera-ready. The staff is kind and always available through text, the beds are soft and squarely stationed in front of a well-appointed bar and flatscreen television, and designer toiletries are filled to the brim. It’s also possible to eat throughout the day at the hotel’s delicious cafe and patio (get the French toast), and then spend the night at its second-floor bar or ground floor lounge. On weekends, even if you’re not a guest, you can stop by for regularly scheduled events including a DJ who spins old and new tunes. If you do plan on leaving the hotel to see the city, then you’re right in the midst of it, and the surrounding neighborhood can keep you readily entertained.

When you stay at the Drake Hotel, don’t be surprised if you feel relaxed, in-the-know, and decidedly cooler once you check out. These are sides of yourself the hotel may have encouraged, but feel free to hold on to them after you return home.

Ontario has another wine destination, Prince Edward County, affectionately named “The County.” This cluster of towns, about 2.5 hours east of Toronto, is home to some of Ontario’s best wineries. But never was there a great place to stay until summer 2015 when Jeff Stober, the hotelier behind Toronto’s stylish Drake Hotel, opened a rural clone, the Drake Devonshire. It’s the ideal retreat for travelers wanting their Drake by Lake Ontario. Once a 19^th-century foundry, the building is now a contemporary farmhouse-cottage, decked out with 11 individually-designed hotel rooms and two suites in the quaint town of Wellington. The property offers coziness all year round in the communal living room and out back over a lakeside fire pit and s’mores. Guests can hang in the barnlike Pavilion for musical performances, sommelier seminars, seasonal events, or just to gawk at the floor-to-ceiling mural by Brooklyn artist FAILE. It doesn’t hurt that Sandbanks Provincial Park—known for its 60-foot sand dunes—is practically the backyard of the Drake Dev.

If it’s not wintertime or you can’t get tickets to see the Maple Leafs play, then the next best way to experience Canada‘s game is by visiting the Hockey Hall of Fame. Situated in downtown Toronto, the museum is located on the lower floor of the Brookfield Place shopping center. It’s a short walk from the CN Tower and other attractions. (If you’re driving, you’ll need to find either metered parking or a parking garage, as there is no designated parking lot for the museum itself.) The Hall of Fame itself contains displays about historic moments in the game’s history, iconic jerseys and memorabilia from players, interactive games for children, and a room where the entire family can get up close with the Stanley Cup trophy.

The Thompson Hotel, Toronto, opened in 2010 as a modern, translucent glass building soaring above its low-rise, red-brick neighbors and staking a claim as a symbol of glitz and glam in the King West neighborhood. Thanks to its fashionable in-house bars and restaurants, the hotel is a popular fixture both with locals and with the Hollywood set who visit each September for the TIFF film festival. The acclaimed Studio Gaia team designed the rooms, which have bold, dark-wood flooring and hot accents of orange playing off cool white walls. Heated marble floors in the bathrooms, spacious tubs, and sheets with high thread counts all contribute to the sense of luxury, and floor-to-ceiling windows ensure that rooms are flooded with natural light. After check-in, guests can use their room key to access the private elevator up to the rooftop bar, with its 360-degree views of the city. The rotating menu of seasonal cocktails is especially delicious.

Tempt fate at the Monkey Paw’s Book-O-Matic machine, where for the price of a toonie you’ll be delivered an archaic tome in the vein of Elementary Arabic, Vol. 3. I’ll let you know how my studying gets on. The Monkey’s Paw is an eclectic vintage bookstore on Dundas with a collection of unique books, vintage maps, and bugs preserved in Lucite.

Located in Leslieville in the East End, Swirl is in a small, converted apartment above a dog store in Leslieville. I love the decor here, from the tables made from doors or antique sewing machine bases to the artwork by local artists FAME. It’s a tiny place but it packs a punch. There’s no kitchen, so they have these amazing appetizers and desserts preserved in small Mason jars. Wine prices are affordable (and they have about three beers available now). On top of all of that, they host theme nights. For instance, you can watch Mad Men whilst sampling accurate cocktails from the era; board game nights; bubbly nights; and cinema Sundays. Suffice it to say, it’s one of my favorites. Warning: it’s tiny in here. Not meant for a big group, but perfect for a date.

Opened in 2006, the Four Seasons Centre for Performing Arts right in the crux of downtown at Queen and University is a gorgeous forum for performances from the National Ballet of Canada and the Canadian Opera Company (COC). For those looking for a frugal experience, the COC holds free concerts most Tuesdays and Thursdays at noon, and some Wednesdays at noon or 5:30 p.m. in the Richard Bradshaw Amphitheatre. Though the National Ballet’s most famous performance is The Nutcracker, performed, of course, during the holiday season, the company also performs other family-pleasing ballets including Sleeping Beauty and Alice’s Adventures in Wonderland from time to time.

Until Toronto hosted the 2015 Pan Am Games, City Hall—two curved modernist office towers that look like a pair of parentheses surrounding a period—lacked tourist allure. But enter a photogenic, rainbow-hued, eye-catching TORONTO sign, and voilà! A star was born. Found in the square directly in front of City Hall, the illuminated sign, originally meant to be a temporary attraction, has become one of the city’s most photographed structures, along with the CN Tower. The sign’s O’s, in particular, are popular with canoodling couples.