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  • 555 Kaukahi St Wailea, Kihei, HI 96753, USA
    Perched 300 feet above the Pacific on 15 verdant acres, Hotel Wailea is a former members’ club that still feels like a hidden enclave of cool. In 2014, new owners invested $15 million in a redesign that left 72 one-bedroom suites with white oak floors, Sub-Zero appliances, and Hawaii-inspired art. Still, it’s the pool that really wins over guests—it’s calm and quiet (thanks to the hotel’s no-kids policy); there are umbrella-shaded loungers and bungalows with fans for when you’ve had too much sun; and the beyond-gracious staff are always at the ready with water, cocktails, kombucha, and coconut water. The hotel lounge offers free wine and appetizers at 5 p.m. on Friday nights, while the farm-to-fork restaurant highlights produce grown in the resort’s own garden. Complimentary on-site activities include yoga, outrigger canoeing, and mixology classes, but guests can take the hotel’s Tesla Model X house vehicles anywhere in Wailea or rent an electric bike and cruise the South Maui coast if they want to get off property.
  • 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.
  • Via Vittorio Emanuele Orlando, 3, 00185 Roma RM, Italy
    Opened by Carlo Ritz in 1894, the St. Regis belongs to a particular category of five-star hotels in Rome in which Old World glamour is alive and well. While the current trend in town is toward boutique hotels and converted townhouses, the St. Regis is palatial and uncompromisingly opulent. In the century (plus) since opening its doors on the crest of the Quirinal hill, the hotel has remained a beacon of luxury, and indeed many of the hotels on the nearby Via Veneto, Rome’s luxury hotel row, take their cues from this long-established pioneer.

    The entrance through the marble portico just off Piazza della Repubblica leads directly into a grand salon furnished with overstuffed chairs, chandeliers, and antiques. The grandeur continues in the rooms, where classic style and sophistication reign. Owing to its elite clientele, the hotel’s 23 suites come with 24-hour butler service, while the aficionado program is designed to provide exclusive access to sites and special experiences including road trips designed by the Ferrari racing team or helicopter rides to wine estates.
  • 600 F St, San Diego, CA 92101, USA
    At first glance, the lobby is the place to be at this boutique hotel in the Gaslamp Quarter. At check-in guests are offered a selection of local wine and beer—and again during happy hour. Under soaring ceilings supported by leather-wrapped pillars and surrounded by colorful art, you can sip and socialize. But don’t ignore the scene on the roof, either, where you’ll find a pool with oversized, floating pillows; fire pits with food and drink service; and views of the Coronado Bridge, Mount San Miguel, and the old and new architectural icons of downtown. In fact, the rooftop is so special, you may want to book the only accommodation in the 159-room hotel that grants you direct access to it: the Cabana Suite, where a private staircase leads to your own poolside cabana. On the other hand, if you’re traveling as a family, you may find that another option beats private rooftop access: the Star Suite, complete with three king-size beds, two of which form a custom-built bunk bed. Either way, expect ultra-modern furnishings paired with skyline views.
  • Sankt Peders Stræde 24A, 1453 København, Denmark
    Noma, consistently ranked as one of the world’s best restaurants, closed in 2016, but its impact on dining in Copenhagen has been profound. Many chefs who worked there have since launched their own restaurants, including two who opened Bror. It’s a small space with big ambitions—expect astonishing food made from the best local produce. The five-course menu costs 625 kroner ($100), with wine pairings an additional 450 kroner ($72). There are also some memorable snacks. Don’t miss the bull testicles with tartar sauce or the cod head with cabbage wrap.
  • Laugavegur 59, 101 Reykjavík, Iceland
    Reykjavík’s Dill restaurant, run by chef Gunnar Karl Gíslason and sommelier Ólafur Örn Ólafsson, is the first venue in Iceland to win a coveted Michelin star. It specializes in New Nordic Cuisine, which means that the kitchen updates traditional dishes such as arctic char, pork belly, and lamb shanks in highly creative and ultradelicious ways—often pairing them with healthy ingredients like barley, berries, and kale. The restaurant is open four evenings a week, and the seven-course menu changes regularly based on availability of local ingredients. Food can be paired with a fabulous selection of champagnes and wines. It’s not the cheapest choice in town, but it is one of the best.
  • 228 W 10th St, New York, NY 10014, USA
    This intimate, 110-seat restaurant has been hailed as one of the West Village’s true gems since it opened in 2008, both due to the chef’s fresh take on classic Italian cuisine and the inviting ambiance the cozy, dimly-lit eatery exudes. An open kitchen grants diners front-row seats to a culinary production with a rotating cast of fresh pastas starring tagliatelle, orecchiette, and garganelli. Seafood also features prominently in the form of charred octopus, roasted cod, scallops or Arctic char. Oenophiles will delight in the extensive list of Italian wines by region, including an impressive 2,500-bottle cellar that also plays host to private dinners. Just be sure and save room for dessert; the buttery olive oil cake flies out of the kitchen every dinner. Don’t have time to make it down to L’Artusi for dinner? The weekend brunch menu is equally divine.
  • Lake Matheson, West Coast 7886, New Zealand
    Lake Matheson is a magical little spot near Fox Glacier. It’s a great place to take a walk at sunset, before enjoying dinner and some local wine at the Matheson Cafe. On a clear day, the reflection in the lake proudly displays all the reasons to be in love with the Westland National Park region of New Zealand, while the rugged peaks of Mount Tasman and Mount Cook rise out of the mountain range. This is glacier country at its best. The lack of wind—the lake is set within the dense rain forest—means Lake Matheson’s surface is calm and still. The reflection photo opportunities have made this lake the most photographed body of water in New Zealand (and that is saying something). The walk around the lake takes about an hour and a half, and you have three viewing platforms offering exceptional perspectives along the way. Hit the trail just before sunset and have a glass of Otago Pinot Noir at the cafe while you watch the sun set over those mountains. The cafe opens at 5:30 p.m. and I’d suggest the mushroom risotto.
  • Finding good Italian food in Asia can be as daunting as Monty Python’s quest for the Holy Grail, which is which why Latteria Mozzarella Bar is so special. The Duxton Hill restaurant boasts nearly a dozen varieties of mozzarella to try, from burrata with roast pumpkin and truffle to smoked buffalo-milk mozzarella with porcini mushrooms. Fish, meat, and pasta mains round out the offerings; savor the homemade red tagliolini with pork sausage ragù, the gnocchi with porcini and truffle cream, or the slow-roasted lamb shanks with chickpeas and red wine. If you’re lucky, you’ll snag a seat on the gorgeous terrace.
  • 3850 Wailea Alanui Dr, Wailea, HI 96753, USA
    A honeymooner’s dream, the 40-acre Grand Wailea hails from the era of the Hawaiian mega-resort. From its perch over the Pacific, the hotel offers an impressive collection of original art (much of it created by locals specially for the property), 40 acres of lush tropical gardens, and over-the-top water features among the nine swimming pools, including slides, caves, a Tarzan swing, swim-up bars, and a canyon with an enclosed “lava tube.” The resort even boasts Humuhumu, a Hawaiian-inspired restaurant set in a man-made lagoon, and 780 guest rooms, all of which include a private patio or balcony. Opt for accommodations on the Napua Club level for a more intimate “boutique hotel within a resort” feel.
  • 501 Southard St, Key West, FL 33040, USA
    Right on Key West’s famous Sunset Pier and next to Mallory Square, Ocean Key is at the center of the action, proven by the flocks of tourists who descend on the pier every evening at sundown. Inside the resort, the contemporary rooms are decorated in tropical colors like bright lime and turquoise, and have bathrooms with rainfall showers and whirlpool tubs and private balconies with views of the Gulf of Mexico or buzzy Duval Street. The angular pool is surrounded by cabanas and day beds; grab a ringside seat for the daily fashion show at Liquid, the kicking poolside bar. Prefer a quieter experience? The spa has a full range of treatments and packages that lean heavily on Asian traditions and ingredients, from Balinese massage to a Javanese rice-and-turmeric body scrub.
  • 111 E Cesar Chavez St, Austin, TX 78701, USA
    Austin has established itself as a foodie destination on par with New York and Los Angeles. Now, it also has a hotel that’s worthy of its rebirth as a capital of cool. At The LINE, the setting is as pretty as the young things who stay there with their stylish pets. The midcentury building houses 428 rooms and suites inspired by the Lone Star landscape, with headboards that evoke desert canyons, blue linens and rugs that nod to Lady Bird Lake (which many of the rooms overlook through expansive floor-to-ceiling windows), and lighting that looks like fireflies in the night sky. The place to be seen is Arlo Grey, where Top Chef winner Kristen Kish serves a menu inspired by her childhood, travels, and Central Texas ingredients—that is until the rooftop bar debuts in fall 2018.
  • Dhar El Mehraz, 30 000، Fes 30050, Morocco
    Contemporary touches meet Moroccan influences at this hilltop escape overlooking the medina. Homemade pastries greet you on arrival in the neutral-hued guest rooms, which balance floor-to-ceiling windows, sleek furnishings, and glass-walled marble baths with brightly patterned rugs, decorative vases, and Moorish lamps. The minimalist hammam is the highlight at the hotel’s Givenchy spa, while the Atlas mountain backdrop serves as eye candy beyond the chaise-lined infinity pool. Should you seek more spirited diversions, a stylish rooftop bar pulses with live music and DJ sets on the weekends. Sip champagne as the sun sets over Fes, then sample local delicacies like quail and almond tagine or roasted cockerel stuffed with raisins and semolina by candlelight at Amaraz restaurant.
  • 11 Yulgok-ro 10-gil, Gwonnong-dong, Jongno-gu, Seoul, South Korea
    Amass Hotel may be located in the heart of one of Seoul’s most traditional neighborhoods, but its interiors are modern and industrial. Black-and-white rooms are compact yet comfortable (think heated floors); opt for a quad room for double the space and a private terrace with a covered long table and benches. The rooftop bar offers views of N Seoul Tower and the city’s skyline, and a downstairs café provides a convenient breakfast option, with many others within walking distance. The nearby Bukchon Hanok Village and Insadong-gil street are shopping hubs for souvenirs, folk art, and handicrafts, and the Changdeokgung Palace is across the street (best to buy tickets in the morning and return later for the tours). The hotel offers free bicycle rentals but is also very subway accessible.
  • 107 Bree St, Cape Town City Centre, Cape Town, 8001, South Africa
    A once quiet downtown thoroughfare, Bree Street now has so many eateries that it is a sort of restaurant row. The feeding starts with breakfast and goes through lunch, afternoon snacks, drinks, and dinner at places like Bacon on Bree, Folk Coffee, the Culture Cheese Club, Café Frank (a must for breakfast or lunch), Clarke’s Bar & Dining Room (very popular for weekend brunches), Chefs Warehouse and Canteen (where it is essential to arrive early because the kitchen closes at around 8 p.m.), and the always packed (especially for drinks) La Parada. Just off Bree Street are many other options, such as the Hungry Herbivore and the House of Machines, whose customers often overflow onto the narrow side street.