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  • 24 Wharf St, Wellington, ON K0K 3L0, Canada
    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 19th-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.
  • 505 College St, Toronto, ON M6J 2J3, Canada
    Bar Raval looks ordinary from the outside, but inside, the sinuous lines of the floor-to-ceiling mahogany woodwork—bar, walls, window frames—instantly bring Gaudí to mind. Created to mimic the spirit of Barcelona’s pintxos bars (in addition to the Catalonian influence of the decor, platters of food are laid out on the bar, as is the Basque pintxos tradition), the space is often packed. In the mornings, patrons sip lattes and enjoy doughnuts finished with a lick of chocolate and spiced hazelnut.
  • 794 Dundas St W, Toronto, ON M6J 1V1, Canada
    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.
  • 170 Rue Saint-Paul O, Montréal, QC H2Y 1Z7, Canada
    Montreal’s very own Prince of Darkness is best known for his mastery of soft, buttery black leather and his play with textures and details such as zippers and horse hair, but he’s expanded his recent collections into a less gothic and more widely accessible styles that have even branched out into color ¬– albeit dark browns and blues. The women’s wear designer has created collections for off-the-rack store Bedo, but to get a real sense of his unique vision and approach to form, best head down to his sleek boutique on chic Rue Saint-Paul in Old Montreal. Here you’ll find statement pieces to be worn to your next gala as well as rugged wear you can integrate into your everyday.
  • 2490 Rue Notre-Dame Ouest, Montréal, QC H3J 1N5, Canada
    Almost unchanged since 1912, the Théâtre Corona (Corona Theatre) in Little Burgundy was built to host showings of silent films accompanied by live music and comedy shows by local troupes. You can still find an orchestra pit and the original dressing rooms under the stage, but since the late 1990s—after coming close to demolition—it has served mainly to host live music, by acts like Buck65, La Roux, and Arcade Fire. The heritage décor, with painted ceiling, gilded columns and heavy jacquard brocade curtains, and the relatively small capacity for 700 spectators, make this a singularly intimate place to see a show. The best sightlines are from the balcony, but there’s nothing like the feel of a smooth wooden dance floor beneath your soles.
  • 698 Eau Claire Ave SW, Calgary, AB T2P, Canada
    A two minute walk from the bustle of downtown Calgary, Prince’s Island Park—which is surrounded by the Bow River—is home to festivals all summer long. The Calgary Folk Music Festival and 52,000 of its closest friends rock and/or folk out on the park the last weekend of July.
  • 34 Avenue Fairmount O, Montréal, QC H2T 2M1, Canada
    Wilensky’s is sort of an institution in the Mile End. Family-owned since its opening in 1932, the place is famous for its extremely cheap snacks, no-nonsense approach, and retro decor. Pressed tin ceiling, Kik Cola clock, ring-up cash register, old-fashioned soda fountain—this place sometimes feels like a time warp or, at the very least, a museum. Perhaps what makes Wilensky’s so special is, incidentally, the Special ($3.90): “All-beef salami with all-beef baloney grilled to mouth-watering perfection on a tasty roll with a hint of mustard.” But don’t try to change anything in it—the owner, Ruth, will not have it. The Special is what it is, and no amount of money will make Ruth change it. Hell, she even wrote a poem about it: When ordering a Special, you should know a thing or two. It is always served with mustard; it is never cut in two. Don’t ask us why; just understand that this is nothing new. This is the way that it’s been done since 1932. Amen to that.
  • 3927 Rue Saint-Denis, Montréal, QC H2W 2M4, Canada
    L’Express, on rue St-Denis in the Plateau Mont-Royal neighborhood, opened in 1980 and has about it the air of a beloved institution. Indeed, with its timeless style, it feels even older than it is. This popular spot serves classic renditions of bistro fare—steak tartare, bone marrow, onion soup—into the early morning hours (2 a.m. except for Sundays, when it closes at 1 a.m.). When the kitchen ventures into new territory, the results are impressive. The spaghetti with mushrooms is unconventional in its presentation (topped with a healthy serving of arugula)—one of those dishes you try on the road and then want to re-create at home. Reservations recommended.
  • 343 Rue Saint Paul Est, Montréal, QC H2Y 1H3, Canada
    Rustic elegance is the order of the day at La Champagnerie, a champagne-only bar in Old Montreal. Between the delicious cocktails, heaven-sent food, and exposed brick walls of this historic building, the drinking experience will be memorable. The menu features over 50 different brands of bubbly (including real champagne, cava, and prosecco) and a very entertaining sabering act, as well as brie poutine and oysters. Contrary to popular belief, la Champagnerie isn’t that expensive. Yes, there is the odd $500+ bottle, but visitors can easily enjoy a meal and a cocktail or two without needing to remortgage their house. A very nice way to spend an evening, if you ask me—champagne, Old Montreal, and good music. Santé!
  • 1425 Rue Jeanne-Mance, Montréal, QC H2X 2J4, Canada
    Ask any Montrealer the question “Which is the fanciest restaurant in town?” and chances are Toqué! will be a frequent answer. Indeed, quite fancy. But also quite expensive. Luckily, chef Charles-Antoine Crête, once mentored by Toqué’s Normand Laprise, decided that a more accessible and younger version of the famous restaurant would fit perfectly well with the new Place des Festivals—in style, location, and ambience. And he wasn’t wrong. I always go for the beef tartare, and not once have I been disappointed. The menu changes according to the season, but there is a constancy in quality, regardless of the time of the year. This is definitely the best way to get a taste of Montreal‘s finest, sans the waiting list and the steep check.
  • 31 Lugard Rd, The Peak, Hong Kong
    If the weather and smog conditions cooperate, the views from the top of Victoria Peak, aka the Peak, will make your day. Go in late afternoon to catch the sunset and then the glittering, lit-up nightscape of Hong Kong. Getting up to Hong Kong Island’s highest point, at 1,800 feet above sea level, is part of the fun. You can always opt for a bus, train, or taxi, but for the best taste of Hong Kong, ride the outdoor (but covered) Mid-Levels escalators, something you won’t find anyplace in the world. It will take about 20 minutes to travel via the series of 20 escalators and three moving walkways up to the Peak Tram, a historic century-old funicular railway that makes the rest of the steep trip to the top.
  • Shop 6132, 19 Dock Rd, Victoria & Alfred Waterfront, Cape Town, 8001, South Africa
    While South Africa isn’t known for its sushi, you can easily satisfy your craving in Cape Town at Willoughby & Co. The menu at this waterfront restaurant is encyclopedic—there’s everything from Boston clam chowder and spaghetti marinara to prawn curry and teriyaki chicken ramen, but sushi is the star. Try the chili-seared tuna sashimi or the tuna roll with caviar sesame seeds.
  • 606 Patricia Street, Jasper, Alberta, Canada
    Stretching a formidable 27 miles, Jasper’s Skyline Trail is a challenge for all but the most seasoned hikers. The journey is worth undertaking—nearly two-thirds of the route is above the tree line, which means you’ll enjoy stunning panoramic views as the rule rather than the exception. The path runs from Maligne Lake back to the town of Jasper at the foot of Signal Mountain, traversing the Maligne Range mountains in the middle. There’s a short window during which you can enjoy this trail, typically from late July until mid-September. The classic trip includes two nights of camping at Snowbowl and Tekarra campgrounds, but if you’re pressed for time, hike like the locals: Many Jasperites choose to start early and finish late, conquering the entire length in a single day.
  • 203 Village Road, Lake Louise, Alberta, Canada
    Reasonably priced food is somewhat hard to come by in the upscale hamlet of Lake Louise, which is why Bill Peyto’s Café is such a find. Located in the HI Lake Louise Alpine Centre hostel and within walking distance of the Samson Mall, Peyto’s has a sizable dining room and an outdoor patio that’s perfect for relaxing on warm, sunny days. The menu is almost as vast as a classic Greek diner’s, including everything from a Thai stir-fry to a traditional poutine, but its dishes are executed flawlessly. (If you’re looking for standard pub fare, you can choose from plenty of burger options.) Servings are generous and cheap, meaning you’ll want to arrive early to lock down a table—especially in the summer.
  • 1500 Orange Ave, Coronado, CA 92118, USA
    The Coronado Bridge links San Diego to Coronado Island—and the present to the past. In the span of just 2.12 miles, you’ll travel from the digital age to a century when “electrified” hotels were practically unheard of. When the Hotel Del Coronado debuted in 1888, its electric lights and telephones made a sensation—as did its resplendence. In 1892, a young guest named Noel proclaimed in a letter to her family back east that “the red and the white between the bluest sky and the bluest water is like a beautiful dream in a fairy story.” Legions of A-listers have checked in ever since, as a who’s who of vintage portraits attests. But while a stay here is delightfully nostalgic—featuring bike rentals, beachside cabanas, and evening clambakes—the 757-room hotel doesn’t live entirely in the past. Take advantage of its upscale spa, spin classes on the beach, and restaurants serving updated takes on coastal cuisine along with creative cocktails. In the historic Victorian Building Suites, you’ll find modern coastal-chic interiors, streaming TVs, and, of course, Wi-Fi. The Beach Village Suites include additional modern luxuries—like a Sub-Zero fridge and dedicated concierge to help you fill it.