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  • 1100 Rue de la Montagne, Montréal, QC H3G 0A1, Canada
    Parisian Brasserie dining, and a few hundred bottles of good wine standing sentinel for good measure. It didn’t take me long to get used to afternoons and evening at La Coupole. I had an equally delightful time at breakfast; a bit of yogurt and granola, some bread and cheese, and NHL highlights from the night before. I’m a simple guy, what can I say. Fine dining, good wine, and hockey fights go together like PB&J. In my book, anyway.
  • 1609 14 St SW, Calgary, AB T3C 1E4, Canada
    With five locations and a well-organized in-store digital database, the friendly staff of family-run Fair’s Fair used bookstore can easily find what you’re looking for, and they have the best selection of popular and hard-to-find books in the city. The cavernous basement of the Ninth Avenue location is for anyone who’s more interested in the journey than destination. They also offer cash for books you want to sell, or twice as much as in-store credit.
  • 6 Powell St, Vancouver, BC V6A 1E9, Canada
    A clandestine spot to imbibe in Gastown, the Diamond is the speakeasy when you’re in Vancouver. Bar none, one of the best bars I have been to on recommendation from Nathan at Judas Goat. They will make you anything here, like a tasty pisco sour. Plus, they give you these really cute glasses with flowers on them. We didn’t try the menu, but if it’s anything like the drinks, I’ll be returning for a meal.
  • 50 Gladstone Ave, Toronto, ON M6J 3K6, Canada
    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.
  • Barnes Bay, West End 2640, Anguilla
    Four Seasons might have spruced up the property slightly when it took over management from Viceroy in 2016, but the original clean lines and sharp angles of the midcentury modern architecture coupled with Kelly Wearstler’s playfully eclectic interiors are still unmistakable at this stunning property overlooking Meads and Barnes bays. Epitomizing tropical modern luxury, the property is awash in marble, natural stone, and wood, with dramatic views of the Caribbean Sea from dining rooms and infinity pools that seem to hover from their cliffside perches. Spanning 35 acres, the resort is home to 166 spacious, serene, and stylish accommodations ranging from suites to townhomes and private villas. Indulge at five dining venues, including the aptly named alfresco Sunset Lounge for sushi and the fine-dining Cobà, where fresh seafood is paired with choice cuts of meat and an impressive wine list. With three swimming pools and two distinct beaches to choose from, the most stressful part of the day is deciding where to lounge.
  • San Fuego 70, 7, Santa Cruz, Aruba
    Day-trippers in search of awesome views, cool drinks, and light bites score at this oasis in the middle of Arikok National Park. The menu is simple and heavy on island favorites, from fried whole fish to seafood served with plantains, salad, and pan bait (a pancake-like bread). There are also hamburgers and cold sandwiches, along with frozen cocktails and local beer. Still, it’s the views that really stun. From its perch between Boca Prins Bay and the Fontein Cave, the restaurant has sweeping vistas of desert, hills, and sea.
  • Ocho Rios, Jamaica
    If you’re looking for a break from the beach and the noise, head to Konoko Falls Park (formerly known as Coyaba River Garden) for a quiet picnic, swim, and nature walk through beautifully manicured gardens. The Mahoe tiered waterfalls—a smaller, just-as-picturesque version of Dunn’s River Falls but rarely crowded—cascade through the park, and an on-site museum showcases the history of Jamaica’s first inhabitants, the Taino. The park offers gorgeous views of Ocho Rios’s bay below. Climbing and swimming in the falls, at your own pace, is great fun.
  • Getting to Portofino from Genoa is quite easy. Take the train from Genoa’s Brignole Station to Santa Margherita Ligure, and then catch the 82 bus to Portofino (a 12-minute trip around the bay). While I’m not a huge bus person, this is one of the most gorgeous bus rides I’ve ever experienced. A tiny fishing village with a very posh clientele, Portofino is a wonderful day trip—perfect for walking around, shopping at high-end boutiques, and enjoying an apertivo dockside before heading back to town. Yet Portofino is also covered with trekking trails, so another option is to wear walking gear and come for the breathtaking hikes!
  • You’ll likely do your sunbathing and swimming on the white-sand beaches of the Grenadines, but St. Vincent’s black-sand beaches are also quite stunning. In Biabou, for example, along the windward coast south of Georgetown, you can stare for hours at frothy ocean waves crashing onto the volcanic black sand. With luck, you’ll also catch a rainbow.
  • Place Jacques-Cartier, Montréal, QC H2Y, Canada
    Running from the waterfront to Montréal’s City Hall, at the opposite end of a gently sloping hill, Place Jacques-Cartier has been a center of the city’s street life for more than two centuries. It was laid out at the beginning of the 19th century after the Château Vaudreuil, which had stood on the site, burned down in 1803. Originally known as New Market Place, the square stays true to those roots with the many vendors who sell flowers here in the summer. You’ll find them on sunny days alongside the outdoor tables of the cafés that line the square. In December, Place Jacques-Cartier is dressed for the holidays with rows of Christmas trees. Given the name of the square, you might expect the column at its western end to be topped with a statue of the French explorer. Instead, the English admiral Lord Horatio Nelson looks over the city from the perch. Erected in 1809, it is Montréal’s oldest public monument and preceded London‘s column honoring Nelson by three decades. To this day, the choice of hero to honor still causes some resentment in this largely francophone city.
  • Mt Lemmon, Arizona 85619, USA
    On the northern edge of Tucson, you can drive through a condensed version of western North America’s ecosystem in about half an hour. On the way up the Mount Lemmon Highway (also known as “Catalina Highway” or “Sky Island Scenic Byway”), you traverse almost all of the different life zones you would encounter if you were to actually drive from Mexico to Canada: starting with the saguaro-studded Sonoran desert, up through grassland, junipers and oaks, pines, and finally a mixed-conifer forest with stands of aspen. You begin at about 2500 ft. and end up at almost 9100 ft. above sea level (about 760 to 2770 meters). In the summer, especially, southern Arizonans love this road: “thirty miles, thirty degrees cooler,” as the saying goes. When it’s 105 degrees down in the city, it’s a perfect 75 up on the mountain. In the winter, you can go skiing in the southernmost ski resort in the U.S.
  • 1615 Main St, Dallas, TX 75201, USA
    While Dallas has never lacked for luxury shopping options—throw a Jimmy Choo stiletto and you’ll hit a designer boutique or upscale department store here—4510’s concept-store format, featuring a well-curated selection of fashion and design pieces from big, emerging, and independent designers, made waves when it first opened in 2000. Since then, the brand has grown to include other outposts in Texas and California, as well as this 37,000-square-foot, four-story flagship in downtown. (The original McKinney Avenue location has been transformed into a home-focused store, and there’s another location in Highland Park Village, too.) Topped by a chic restaurant and filled throughout with artwork, the store continues to feature women’s and men’s fashions, home decor and furnishings, jewelry, and beauty products by labels known for creativity and craftsmanship. The lineup varies, but you can be sure the selection will be thoughtful and fun, and that many of the pieces will be one-of-a-kind or newly available to retail—ensuring that you’ll leave with something special.
  • Skomakaregatan 11, 211 34 Malmö, Sweden
    Leave it to the coolest, hippest country on the planet to come up with a cool concept like that. Sweden, you keep surprising me. Imagine a ultra-modern record shop in the heart of a touristy, busy medieval square. Imagine a mouth-watering café that offers cakes each more delicious than the other, and a plethora of imported coffee. Imagine a fabulous soundtrack, that goes from the classic grunge hits to the indie Swedish hits. This place is called Folk A Rock - it’s an ode to rock music that shares a passion with traditional fika and appreciates the beauty of its historical neighborhood. I’ve never seen anything quite like it - not that I would expect to. Sweden, in all things fashion, music, and, well, just about anything really, has a secret recipe for these types of things that few can rival. These über, effortlessly cool types of things. One one hand, it kind of makes you want to hate Sweden and remain green with envy. But on the other hand, the result is always way too fun to overlook, especially in the case of Folk A Rock. If you’re an indie music lover with a sweet tooth, this may just be your heaven on Earth.
  • 1 Rue des Carrières, Québec, QC G1R 4P5, Canada
    Set high above the St. Lawrence on Cap Diamant, overlooking Old Québec, this imposing yet inviting landmark is as much a lodging as it is a tourist attraction, borne out of its reputation as the most photographed hotel in the world. Opened in 1893 by the Canadian Pacific Railway to drum up luxury riders for its trains, the castle-like Fairmont Le Château Frontenac feels every bit as grand today as it must have when Roosevelt and Churchill secretly hatched plans for the invasion of Normandy here in 1943—and it continues to be the hotel of choice for A-list celebrities and other notables. A $75 million renovation in 2014 updated the 611 rooms with a more contemporary feel, draping spaces in chic furnishings and soothing shades of gray and cream, plus butter-yellow or soft turquoise accents. The spa features seven treatment rooms adjacent to an indoor pool, whirlpool, steam rooms, and a gym, but the hotel has become a destination for its food: Champlain restaurant is helmed by acclaimed young chef Stéphane Modat and offers a modern take on Québécois cuisine alongside magnificent views, while 1608 Wine & Cheese Bar highlights local wines, cheeses, and charcuteries.
  • 10100 Dream Tree Boulevard
    More than four decades after Walt Disney World welcomed its first guests, the Four Seasons opened on 26 acres a few miles south of the Magic Kingdom, finally giving parents a true luxury resort option within the park. Well-sized and well-appointed rooms are typical of the brand’s understated elegance, but expect to pay a premium for a room with a balcony overlooking Disney’s nightly fireworks (or just reserve a table at the top-floor Capa steakhouse). Kids get the luxury treatment, too. The resort makes it easy for guests to organize park visits right on site: The Disney Planning Center helps with tickets, handles extended Magic Hours and Fast Pass requests, and books restaurant reservations and transportation to the monorail station and the rest of Disney World. Serious fans can also have a photo op with Goofy and friends at the resort’s character breakfast. A giant pool with a lazy river and two waterslides beckon on days when you’d rather not brave the park crowds, and children get dedicated welcome amenities, toys, and costumes during their stay. The extensive menu of spa services even includes a princess-themed mommy-and-me makeover treatment, including a tiara and wand.