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  • 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.
  • New York, NY 10018, USA
    A few green acres of valuable Midtown Manhattan real estate affords office workers and visitors with valuable peace and space, two things that are hard to find in the surrounding streets. Bryant Park shares the block between Fifth and Sixth avenues and 41st and 42nd street with the main branch of the New York City Library (also worth a visit). The library runs an al fresco reading room along the north end of the park, and occasionally hosts readings and author events. In summer, a stage at the western edge of the vast green lawn runs a busy schedule of performances and films. In winter, the lawn becomes an ice skating rink and the site of a busy holiday market. All year round, the park is a popular destination for the bocce ball courts, ping pong tables, small carousel, food kiosks, open lawns, gravel paths, seasonal plantings, and a graceful fountain. It may be a challenge to find a seat at lunchtime, but it’s worth the wait. Take a break from your walk and enjoy some great people-watching, as well as shade and a measure of serenity in a green space bound on all sides by tall buildings.
  • 7070 Avenue Henri-Julien, Montréal, QC H2S 3S3, Canada
    After Toronto, Montréal is the Canadian city with the largest population of residents of Italian descent. For more than a century, the community has been centered in one of the city’s most charming neighborhoods, Little Italy. The way to the heart of this neighborhood is arguably through its stomach or, rather, the Jean-Talon Market, where residents have come to buy produce and stock their pantries since 1933. Even if you aren’t shopping for fresh vegetables or fruits, it’s a good place to come to sample Québecois products and buy gifts like local jams, jellies, and maple products to take back home.
  • Calle Quinta Avenida, Playa del Carmen, Q.R., Mexico
    Playa del Carmen’s winning charm emerges all along this wide pedestrian avenue, which runs parallel to the beach. Eateries here include everything from cheap fast food like Pizza Renzo to upscale restaurants and cafes; the best people-watching is from outdoor seating at the sports bar Tequila Barrel or Chez Céline bakery. The shopping scene offers international luxury brands side by side souvenir shops, but the most interesting Mexican handicrafts await at boutiques like Sin Pecado and Sol Jaguar. Since this part of town has little shade, it’s best to avoid the midday sun; instead, try an early-morning visit with some streetside coffee in hand, then revisit at sunset to kick off an evening of dining, shopping, and bar-hopping.
  • 210 Main Road, Joe Batt's Arm, NL A0G 2X0, Canada
    This hotel is on our list of The 10 Best Hotels in Canada.

    Fogo Island Inn sits at the very edge of the north Atlantic on isolated Fogo Island in Newfoundland. Designed by internationally renowned architect Todd Saunders, the inn’s arresting modern appearance is suggests an iceberg from a distance, with its raised section representing the island’s traditional stilted fishing platforms. But when visitors get close, they see the wooden boards layered together, and it’s clear that everything is handmade. The by-hand ethos covers all the furniture and furnishings, created by local artisans who’ve worked with artists in residence to create contemporary versions of traditional objects.

    Staying at the inn is admittedly expensive, but this is essentially a living art piece that supports the local community and aims to honor the island’s past while carrying it to the future. It feels like a grand home with attentive staff. A private 42-seat cinema, partnered with the National Film Board, carries a movie library for guests to enjoy at any time; there’s also an art gallery, a well-stocked library, and a supply of Gore-Tex hiking boots and other outdoor equipment to borrow. The inn shows off the dazzling landscape, and it’s easy to spend all day at the windows watching the sea while whales breech, icebergs float past, or storms dash on the rocks.
  • 801 W Georgia St, Vancouver, BC V6C 1P7, Canada
    This hotel is on our list of The 10 Best Hotels in Canada.

    Originally opened in 1927, Vancouver‘s Hotel Georgia was the celebrity haunt of everyone from Elvis and the Rat Pack to Errol Flynn and Katharine Hepburn. The hotel closed in 2006 for a multimillion-dollar restoration project and reopened as the Rosewood Hotel Georgia in 2011. Elvis may have left the building, but the old-school glamour remains—with a modern twist. The spacious rooms glow with a soft palette of warm gold, vanilla, and cocoa. Rain showers, heated marble floors in the bathrooms, and fine linens add to the hotel’s luxury appeal. The wood-paneled lobby buzzes with guests and locals en route to the acclaimed Hawksworth restaurant. The hotel has a large private art collection and there are pieces on display from founders of Canada’s modern art movement and famous international artists; the reverse-perspective Patrick Hughes piece opposite the reception desk is fantastic—walk back and forth to see the painting “move.” At the gleaming bar, guests can try the Hotel Georgia cocktail—a modern take on the original Prohibition-era recipe.
  • 11 E Walton St, Chicago, IL 60611, USA
    This hotel is on our list of The 11 Best Hotels in Chicago.

    Designers Lisa Simeone and Gina Deary of KTGY Simeone Deary Design Group oversaw the original design of the Parisian-inspired Waldorf-Astoria Chicago in 2009, and the pair was once again brought in to breathe new life into this 215-room Gold Coast gem. Rooms are now bright white, well-lit, and include pops of uplifting magenta. Before you hit any of them, however, there’s much to entice at street level. Enter from the circular driveway and marvel at the Swarovski chandelier, modeled after a vintage brooch, along with the herringbone wood floors and black-and-white pinstriped stone. Don’t miss the Peacock Lounge and its secret sister, Bernard’s Bar, an intimate craft cocktail and champagne boîte, which is virtually unknown even by city denizens (which means you can always find a seat). Its Scottish and equestrian themes are almost as anachronistic as the Mansard roof and circular driveway, which just adds charm to this newly beloved Chicago hotel.

    The guest rooms feature oversize headboards and abstract floral bedspreads, while bathrooms are a marvel of marble. For something more, splurge on either the new 1,800-square-foot Astoria Suite or the redesigned 2,400-square-foot Presidential Suite, both of which will have you feeling you’ve been transported to a Parisian pied-à-terre (the latter’s primary bedroom features a fireplace).
  • Adjacent to Romney Manor and the Caribelle Batik factory, Wingfield Estate is a former sugar plantation dating back to the mid-1600s. Here, you’ll find ruins of the rare St. Kitts sugar mills, which were powered by water instead of wind. Also on-site are the remains of a stone chimney, a distillery, and an aqueduct system that brought water from the Wingfield River down the slopes of Mount Liamuiga.
  • Tržiště 9, 118 00 Praha 1-Malá Strana, Czechia
    Prague’s centuries-old connection to music survived occupation by both the Germans and the Communists, so it’s fitting that those deep roots strike a chord at Aria Hotel Prague, where all of the rooms are named after famous composers or singers, from homegrown sons like Dvořák and Smetana to contemporary icons like the Beatles, Ella Fitzgerald, and Elvis Presley. The hotel even has a music director who can point you to the city’s best performances, as well as assist with suggestions in the music library; guests borrow CDs or concert DVDs to watch in their rooms, which are all outfitted with hi-fi sound systems that include Marantz speakers, plus flat-screen TVs, Blue-Ray players, iPads, and Apple TVs. All 51 accommodations were given a head-to-toe makeover in early 2018, resulting in sumptuous rooms decorated in shades of soft peach, dusty rose, and sandy taupe, and combining a pleasing mix of antiques and modern furniture. During summer, the superb CODA restaurant commands stunning rooftop views, while the Winter Garden Atrium is cozy perfection in colder months with its piano recitals accompanying afternoon tea or wine.
  • 100 E San Francisco St, Santa Fe, NM 87501, USA
    With its historic pueblo-inspired architecture and Spanish Revival style, this landmark Santa Fe hotel looks like it dates back much earlier than 1922, when it was designed by two of the area’s top architects: Mary Elizabeth Jane Coulter and John Gaw Meem. And, in fact, despite the imposing building’s relative youth, the legacy of La Fonda dates back to the 1600s. An inn or hotel has stood on this site since the city’s founding at the end of the Santa Fe Trail.

    Now, as one of the city’s most iconic luxury hotels, it presides over the historic Plaza and boasts some of the best views of the city and surrounding mountains and desert. Thanks to a complete (and completely faithful) renovation in 2013, rooms are now bright and airy, outfitted with handcrafted furnishings, local artwork and textiles, energy-efficient casement windows, and all the luxuries expected of a modern grande dame. The fine-dining courtyard restaurant is one of the most romantic dining destinations in town—trumped only by the rooftop Bell Tower Bar, whose sunset views and margarita menu draw locals and in-the-know visitors alike. Throw in a heated outdoor pool (open year-round, a rarity in Santa Fe) and a decadent spa, and it’s no wonder that La Fonda has maintained its reputation for superlative hospitality for so long.
  • 2727 Indian Creek Dr, Miami Beach, FL 33140, USA
    When Freehand launched in Miami at the end of 2012, it became a welcome alternative to the city’s glitzy hotel scene. The retro-inspired, summer-camp-style hotel is housed in a 1930s building outfitted with vintage furnishings and wood paneling by New York design firm Roman and Williams. Laid-back activities (art classes, yoga) encourage mingling, while the Broken Shaker cocktail lounge has become a local hangout and earned two James Beard Award nominations.

    Freehand Miami bills itself as “a hostel for a new generation of travelers.” Indeed, a visit here confirms that it’s very far from the stereotypical dingy hostel. In fact, were it not for the shared rooms, the Freehand would likely fall into the “boutique hotel” category.

    Room decor includes vividly colorful modern art and Mexican blankets, and free Wi-Fi is available. There are also private rooms that come with work desks and flat-screen TVs. The complimentary breakfast is popular with guests and includes Cuban pastries and locally roasted Panther coffee. Evenings are well-spent at the hostel’s on-site bar, the Broken Shaker, which in 2014 was listed #22 on Drinks International’s World’s 50 Best Bars list. It specializes in inventive “garden-to-glass” cocktails, which blend familiar spirits with unique homemade bitters and ingredients that aren’t usually found in cocktails, such as green bean juice.
    One could argue that the stylish, affordable hotel trend was actually ushered in by a pop-up craft cocktail bar in the courtyard of a defunct historic hotel just north of the South Beach fray. Five years later, The Broken Shaker is a permanent fixture of Miami Beach nightlife and the anchor of The Freehand Miami, a hip hotel-cum-hostel with both private and shared rooms designed by Roman & Williams in a subtle nautical theme. It’s also home to 27 Restaurant serving seasonal farm-to-table fare inspired by Miami’s melting pot of cultures. Perennially popular amongst locals, it should be at the top of every traveler’s list. The concept’s proven such a hit that they’ve recently opened hotels in Chicago and L.A. with New York on the horizon.


    What was once a pop-up bar, The Broken Shaker is now a permanent fixture at the Freehand Miami. The James Beard Award-nominated bar is located in the high-end hostel on South Beach serving up a selection of handcrafted cocktails. The bar itself is a tiny room by the pool with a 1950s Havana look. You can grab your cocktail—made with elixirs, syrups and infusions using herbs and spices from the onsite garden—and drink it in the bar, or head outside to the pool and nestle into one of the lounge chairs. Away from the hustle and bustle of South Beach, The Broken Shaker offers a more intimate setting than the lavish pools at high-end hotels in the area.
  • 540 Park Ave, New York, NY 10065, USA
    A staple among Upper East Side hotels since it opened in 1963, the sophisticated Loews Regency boasts a Park Avenue address and location convenient to Central Park and Manhattan’s best museums. Following an extensive renovation, it reopened as a fresh and chic retreat in early 2014. The bones of the hotel remain classic, but the approach is modern, with touches that today’s traveler will appreciate, such as free Wi-Fi. Its elegant lobby—with a striking art installation from Brooklyn artist Nina Helm—impresses with its 24-foot ceilings and the on-site salon and spa, from acclaimed hair stylist Julien Farel, is a neighborhood destination for visitors and locals alike. No classic New York hotel would be complete without a standout watering hole; you’ll want to order a cocktail at the low-lit Regency Bar.
  • Am Wriezener Bahnhof
    This club, housed in an old industrial warehouse, does not look unlike a mental ward and, inside, has as many fascinating levels as an Escher drawing. To dance with a sea of the coolest kids in Berlin (and Europe for that matter—it’s a landmark destination for partiers across Europe), stay on the ground floor. For a smaller scene, head to the top floor, which gradually attracts a more queer crowd as the weekend goes on. That’s the other thing: it’s only open from Friday until Monday morning. Wear plain clothes and no smile to get past the doorman. If at first you don’t succeed, come back on Sunday nights when the line is shorter and the bouncers are known to be less prickly.
  • Shop #10, 26, Hope Rd, Kingston 10, Jamaica
    When in Kingston, make time for a stop at Devon House, a grand 1891 Georgian mansion that was built for George Stiebel, Jamaica‘s first non-white millionaire. The lovely upright house and its 11 surrounding acres are now protected as a National Heritage Site, but that doesn’t mean that there’s not fun to be had. The sprawling grounds include shops, restaurants, a bakery, and a popular ice-cream shop, I-Scream. House tours can be arranged, but the grounds, landscaped with stately palms and fountains, are the highlight—it’s a great spot to take a stroll, read, shop, or dine. The mansion and its manicured lawns are also used for weddings and lavish events.

  • 155 W 51st St, New York, NY 10019, USA
    Le Bernardin, on 51st Street between Sixth and Seventh avenues, is one of the handful of New York restaurants that is regularly awarded four stars by the New York Times (it is also one of five restaurants in the city with three Michelin stars). Chef Eric Ripert’s specialty is fish, and the menu is divided into three categories: “almost raw,” “barely touched,” and “lightly cooked.” If you like your tuna cooked medium, this isn’t the right place for you. Ripert often finds his inspiration in Japanese cooking, with his sashimi and light broths, and adds some Latin American influences, in his ceviches and some other dishes. The fish is always allowed to take center stage, and typically any sauce is merely intended to accent its flavors. The dining room has an understated, contemporary style with light-wood walls and high ceilings. Unlike some celebrated chefs, Ripert has chosen not to build a restaurant empire, increasing the odds that on any visit he will be at Le Bernardin, presiding over its kitchen and dining room.