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  • 4175 Boul St-Laurent, Montréal, QC H2W 1Y7, Canada
    Not to be mistaken for the popular izakaya of the same name (and same owners) down the street, on Boulevard Saint-Laurent and Avenue des Pins, this Big In Japan is on the corner of Boulevard Saint-Laurent and Rue Rachel. You may not notice the sign, or even the door – it adds to the sense of mystery of this high-class drinking establishment (look for the black door near the fast-food restaurant Patati-Patata). From the vaporous curtains to the long shiny U-bar, the atmosphere here is distinctly speakeasy, and the classic cocktails maintain that illusion. The champagne cocktail will never go unwanted, and the Tom Collins is fizzy and tart, as it should be. Or you could dip into the house specialties: sakes, prune wines and Japanese whiskeys, used bottles of which serve as the basis for this stylish spot’s contemporary lamp fixtures.
  • 550 Wellington St W, Toronto, ON M5V 2V4, Canada
    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.
  • 5300 Boulevard Sainte-Anne, Québec, QC G1C 1S1, Canada
    Under 20 minutes by car from Québec City (or, if you are feeling ambitious, less than an hour by bike, with most of the ride on a well-maintained path), Chute-Montmorency (Montmorency Falls) is the area’s most impressive natural wonder. If you visit the Musée National des Beaux-Arts du Québec before you go, the sight will look familiar: Montmorency has long been a popular subject for local painters. Think Niagara is impressive? The cascade here is a full 99 feet higher—272 feet to the Horseshoe Falls’ 173 feet. In winter, spray from the falls freezes into a hill at its base, known as the Sugarloaf, and snowshoes are available for rent if you want to explore the nearby trails. In the summer, there’s a zip line for those in search of an adrenaline bump. Year-round, a cable car carries passengers to the top of the falls, providing bird’s-eye views en route.
  • 30 Mercer St, Toronto, ON M5V 1H3, Canada
    Tucked away on a side street between King Street and Blue Jays Way in the heart of Toronto’s entertainment district, Hotel Le Germain is a cozy escape from the bustle of the city. The lobby has a library area where guests can curl up on sofas and, in wintertime, enjoy the atmospheric crackling of the wood-burning fire. In summer, the rooftop putting green on the 11th floor is the place to relax. Following a full renovation project in early 2015, the minimalist rooms are monochrome with colorful accents, and the generously sized bathrooms have glass-walled rainfall jet showers. The hotel piles on a raft of extras, such as free Wi-Fi, newspapers, and in-room Nespresso coffee machines. There is also a complimentary breakfast that includes croissants and pastries.
  • Dawn Beach, Sint Maarten
    For those wanting an active adventure on the water, Captain Alan’s Boat Charters offers snorkeling as well as clothing-optional boat trips. Their Snorkel and Beach excursion allows you to experience four hours of snorkeling and swimming around St. Maarten, Pinel Island, and the uninhabited Tintamarren while riding in one of their 30- to 38-foot off-shore power boats. Enjoy a swim with tropical fish and sea turtles, and then head back onto the boat for snacks, an open bar, and music. Captain Alan’s Boat Charters also offers a 6-hour adventure, trips to nearby Anguilla and St. Barth’s, and a clothing-optional nude cruise.
  • 818 S 2nd St, Minneapolis, MN 55415, USA
    Although the new Guthrie Theater was only completed in 2006, it has a rich history in the resident-theater movement of the 1960s. Architect Jean Nouvel created this stunning masterpiece that is worth visiting even if not attending a show, although attending one would be ideal. The space has three, differently sized theaters, and the “Endless Bridge” lobby extension leads to panoramic views of the Mississippi River, Stone Arch Bridge, and St. Anthony Falls.
  • 76 Queen St, Charleston SC
    At this Charleston hit, James Beard Award–winning chef Sean Brock reinterprets traditional Southern dishes with a steadfast commitment to local and regional ingredients—the restaurant even has its own garden. Constantly changing, the menu is filled with inventive new takes on Southern cuisine, such as pig’s ear lettuce wraps done up “buffalo” or “Kentukyaki” style.

    Don’t miss the Carolina Grouper—it’s one of the most beautiful dishes at this establishment, and a regional classic you have to try while visiting Charleston.

    Note that the restaurant also has locations in Nashville, TN and Savannah, GA.
  • 744 Front St, Lahaina, HI 96761, USA
    Fleetwood Mac front man Mick Fleetwood is behind this bar and restaurant, located on a third-floor rooftop in Lahaina. Here, guests sip drinks under beige umbrellas while taking in views of the dreamy blue Pacific. To pair with award-winning cocktails like the Heart of the Jungle (Cynar, Velvet Falernum, coconut rum, and lemon juice), which comes in a tiki artichoke, executive chef Eric Morrissette serves a menu of elevated bar bites, fresh local fish, and meatier dishes like filet mignon with peppercorn reduction. If you’re not a cocktail person, know that the robust drink menu also features beers from Maui Brewing Co. and Kohola Brewing as well as exclusive wines like Krug Brut from Reims, Luberri Gran Reserva rioja, and even a Chateau Musar red blend from Lebanon.
  • 1 Main St
    Tucked away on an eight-acre estate at the top of St. Helena’s main street, Harvest Inn could easily be mistaken for a private country manse somewhere in England, or even northern France. Its lush gardens are traversed by winding pathways, and its brick-accented, Tudor-inspired architecture suggests somewhere far more Old World than upstart Napa. Even its sinuous pools and cozy rooms (many with fireplaces and private outdoor hot tubs, mind you) are reminiscent of a style somewhat less rustic-chic than tends to be in vogue here in wine country. Indeed, by Napa Valley standards, the intimate inn is part of the old guard, its original 25 rooms dating back to 1975, just after the famed Judgment of Paris tasting brought the region’s New World wines into the international spotlight.

    But the Harvest Inn is no less luxurious than the new resorts popping up all over Napa Valley. It has one of the most desirable locations in one of the most desirable parts of the world, surrounded by celebrated vineyards and presiding over arguably the most picturesque town in wine country. It also features a popular restaurant, Harvest Table, which serves dishes full of ingredients from the hotel’s on-site vegetable and herb garden.
  • Diez de Sollano y Dávalos 16, Zona Centro, 37700 San Miguel de Allende, Gto., Mexico
    Local chef Donnie Masterton long ago refined the art of matching sensory experience to fine food, and The Restaurant, on Sollano in the Centro, offers thrills on every level. Dinner here is an occasion for shirts with collars for men and shoes otherwise reserved for dancing for the women. (Dancing, by the way, often erupts in the bar in the wee hours, so it’s good to be prepared.) And while every night at Donnie’s proves a visual treat, Thursday nights are the see-and-be-seen scene, when locals stop in for gourmet burgers—available that night alone—with their Chateau Puy Blanquet St. Emilion Grand Cru.
  • 1415 1st Ave, Seattle, WA 98101, USA
    You really can’t ask for fresher beer than they serve at the Pike. This huge pub is actually built around the equipment that is brewing the next batch as you drink. It’s the brainchild of Charles Finkel, whose passion is evident in this glorious shrine to beer, with his collections of bottles, ads and vintage merch covering every square inch of the place. When we visited, he was actually putting up some beer-themed stamp collections on one of the few remaining patches of uncovered wall; we got chatting, and in his enthusiasm he insisted on taking us down to the basement for a tour of the workfloor. Charles just adores what he does and you can taste it in the microbrews, a selection of lovingly crafted beers that you’ll struggle to find outside the Pacific Northwest. I loved “Naughty Nellie,” a golden ale that slips down rather too easily, but there’s more than a dozen types to choose from not to mention seasonal varieties (we visited at Halloween, when a special Pumpkin ale was on tap). A good way is to buy the tasting menu, which includes around eight of their flavours (although beware, some of them are fairly strong and might go to your head). The Pike’s easiest to find if you approach it from 1st Avenue, through Pike Place Market, although we stumbled onto it in Post Alley, where you can get an elevator up to the pub. We stumbled upon it when we were just gasping for a drink—but we got so much more.
  • Grace Bay Road, Providenciales, Turks and Caicos Islands
    Housed on a 1,100-foot stretch of beachfront, Grace Bay Club is as stylishly current as it was in 1993, when it became the first luxury hotel to open on the then nearly empty sands of Grace Bay. From its original 21 rooms, the upscale property has grown to 82 suites, each of which features ocean views, a private veranda or patio, and chic interiors by renowned designer Thom Felicia. Guests can also look forward to superior service, including a personal concierge available day or night via a provided cell phone.

    When hunger strikes, there’s the oceanfront Infiniti Restaurant & Raw Bar, which boasts sea-to-table fare and the longest bar in the Caribbean, as well as several other family-friendly venues, including The Grill. If it’s pampering you seek, make time to visit the spacious Anani Spa, where you’ll find six treatment rooms, including one just for couples. A spa tent is also available for beachfront massages.
  • 219, ave. Mont-Royal Ouest, Montréal, QC H2T 2T2, Canada
    With a playful menu divided into sections named “warm-up,” “game,” “set,” and “match” sections, Le Filet volleys some exceptional dishes at guests. Opened in 2011, the restaurant specializes in seafood but does an equally good job with meat dishes, including duck and venison. It comes recommended highly by Ritz-Carlton concierge Simon Bajouk.
  • 4910 Rue Sherbrooke O, Westmount, QC H3Z 1H3, Canada
    You’ll want to spend hours in this cheerful second-floor boutique, trying on everything in sight with the help of the knowledgeable staff. The unique collection of goodies includes Montreal fashion brands like Pajar alongside international favorites including Citizens of Humanity, James Perse, J Brand and Free People. The seasonal lookbook is casual, sophisticated, adaptable and fresh, with a focus on natural, flowing textiles and muted colours, with a few punches of high-octane hues. The accessories collection alone is worth the trip, especially the handbags.
  • Carlisle Bay, P.O. Box 288 St. John's, Old Rd, Old Road, Antigua and Barbuda
    Opened in 1962, Curtain Bluff is Antigua’s oldest luxury resort, and one of the island’s finest. It is the kind of place guests return to through the generations, with the same expectation of timelessness they’ve experienced for as long as they can remember. Located at the southern end of the island on a promontory that divides an often roiling Atlantic from a much calmer bay, the resort offers sea views from every room, two beaches, a top-notch tennis center, a pair of restaurants that can boast one of the Caribbean’s most outstanding wine cellars, and a staff whose commitment has often been passed from parent to child. And except for spa treatments, a premium bottle of wine, and the occasional Cuban cigar, there is little that’s not included in the rate, making a stay a better value than the price might at first indicate.