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  • 50 W Washington St, Chicago, IL 60602, USA
    The second most famous public sculpture in Chicago is 50ft high, made of steel and no one knows what it means. It’s doesn’t even have a proper name so it’s just known as “The Picasso.” Pablo Picasso gifted this untitled sculpture to the city of Chicago in 1967 and it caused a big ruckus because, well, it’s weird looking and no one knew what it was supposed to be. A woman? A chimera? A face? Hard telling. We do know that it was the first modern sculpture installed in the downtown area and it’s now the pride and joy of Chicagoans and photographed almost as much as the Bean. On sunny days you’ll see kids sliding down that sloping steel base and I love that the city still allows those jungle gym antics on such famous real estate.
  • San Ignacio, Belize
    Rolson’s Hotel and Restaurant is high on a hill, overlooking the town of San Ignacio, not too far from the ruins of Cahal Pech. The restaurant’s tables are mostly outdoors, and the view provides a wonderful backdrop to meals that showcase the best of Belizean and Mexican cuisine. My favorite was a chicken burrito drowning in cheese and salsa. I also thoroughly enjoyed the horchata, fresh-squeezed lemonade and michelada. At happy hour, Monday through Friday between 5 and 7 p.m., the michelada is a welcome refresher. Wireless Internet is available, making Rolson’s a great place to get some work done while enjoying wonderful food served with a smile. The longer you linger, the merrier the atmosphere becomes, as locals seem to favor enjoying a late dinner on Rolson’s breezy patio. Dinner is served from 6 to 10 p.m.
  • Kasteleinsstraat 49, 1050 Elsene, Belgium
    The Contemporary Art scene in Brussels is thriving, but it can also be intimidating to newcomers. Many galleries can feel cold or stuffy, and visitors can be put off by the high prices of the works on display. Maison Particulière is a different kind of gallery. Here, nothing is for sale and the space is warm and inviting. Visitors are encouraged to relax on comfortable furniture and enjoy the art as if it was in their own homes. The art on display is on loan from private collectors, passionate about sharing their art with the public. They choose which of their works to include, based on a particular theme. Each room, in this beautiful gallery, reflects the personality of the individual collector, and stepping inside is like taking a peek into their own private world. Maison Particulière makes contemporary art feel accessible and demonstrates how you can live with art in a non-confrontational way.
  • 71895 CA-1, Big Sur, CA 93920, USA
    For such a remote region, Big Sur has more than its share of amazing places to stay. One of the most unique is Treebones Resort, nestled high in the foothills of South Big Sur overlooking the Pacific. The off-the-grid property offers 16 signature yurts as well as oceanfront campsites, a 500-square-foot “autonomous tent,” and the “human nest,” a spherical dwelling woven from tree branches by local artist Jayson Fann. Even nesters have access to the resort’s pool, hot tub, and restaurant, which highlights produce from the on-site organic farm and houses what has to be one of the world’s most scenic sushi bars.
  • 1250 Bannock St, Denver, CO 80204, USA
    Clyfford Still brought new energy to the art world after World War II with his large-scale, color-splashed paintings, and is considered one of the most important American artists of the 20th century. Though his influence on the Abstract Expressionism movement was at least as important as that of contemporaries Jackson Pollock and Mark Rothko, Still eventually broke all ties with the art world after moving to a farm in Maryland, and following his death in 1980 a huge collection of his work was sealed off completely for more than 30 years. His is widow donated his pieces to the city of Denver in 2004, and in 2011 the Clyfford Still Museum opened, housing 94 percent of his life’s work, including some 825 paintings on canvas and 1,575 works on paper, as well as sketchbooks, journals, and his library—in a museum considered one of the best examples of contemporary architecture in the city.
  • 3801 Discovery Park Blvd, Seattle, WA 98199, USA
    Seattle’s largest public park sits on a sea bluff that’s high enough to pierce the city’s infamous fog, revealing gorgeous views of the Cascade and Olympic mountain ranges. Wander its 11 miles (18 km) of paths through forest groves, meadows fringing coastal cliffs, and active sand dunes on the protected tidal beaches. Once a military installation, the area now serves as an open space and wildlife sanctuary. Stop into the Daybreak Star Center, which celebrates American Indian culture and hosts the city’s powwow in mid-July. Around 25 drum groups and 500 dancers converge here for the event, along with close to 10,000 spectators.
  • 4070 S Avenida Saracino, Hereford, AZ 85615, USA
    Last April, I spent a morning hiking along the San Pedro River, just NW of Bisbee, AZ; the caterpillars were astoundingly abundant. When I stopped, I could hear them munching on leaves all around--a surround-sound of crunching, the aural fecundity of spring. Between Sierra Vista and Bisbee, the high grassland highway slowly slopes down to this cottonwood-lined river--one of the few free-flowing rivers left in the Desert Southwest. This ribbon of forest stretches from the Mexican border up towards the lower-elevation desert, providing a flyway for migrating birds and even habitat for the occasional jaguar (very rare). In the late 1980’s, this area was made a National Conservation Area, and it’s a nice shady walk in what can often be sun-blasted country.
  • Parrot Cay Turks and Caicos Islands, TKCA 1ZZ, Turks & Caicos Islands
    Some 35 minutes by boat from Providenciales, sitting all alone on a 1,000-acre island with three miles of white-sand beach, Parrot Cay attracts a seriously moneyed clientele who care, more than anything, about its exclusivity and its spa. Parrot Cay is not exactly monastic: the long list of celebrity visitors has included Jennifer Garner and Ben Affleck (they got married here), as well as Paul McCartney, Julia Roberts, Jerry Seinfeld, and Liam Neeson. But the spa, COMO Shambhala Retreat, is so successful at projecting a holistic way of life that a sense of peace and harmony embraces the entire resort. The central garden-view and ocean-view rooms, three minutes’ walk from the beach, are acceptably chic, but the beachfront suites and villas are knockouts, and the handful of private homes for rent, some owned by celebrities (Christie Brinkley, Donna Karan), are in the fantasy category. The food, by a chef whose résumé includes a Michelin star, and the service, performed by private butlers for some room categories, are of commensurately high standards.
  • Viale Piave, 1, 20129 Milano MI, Italy
    Italy’s No.1 chef Massimo Bottura described Nottingham Forest as a blend of “Hemingway and the TV show C.S.I.” for its eclectic vibe. But for its cocktails, Bottura and many others feel Nottingham Forest is Milan‘s main innovator. Mixologist Dario Comini just happens to be considered one of Italy‘s best bartenders, thanks to a great mix of creativity and risk.
  • Bremerholm 6, 1069 København, Denmark
    A five-star property in an old transformer station, Hotel Herman K brings industrial-chic style to the heart of Copenhagen. Much of the building’s raw, unpolished architecture has been preserved, lending the hotel an edgy vibe. A façade of dark bronze slats and large glass doors leads to the lobby, where a custom-designed artwork by Pio Diaz hangs from 40-foot ceilings. Down moody, dimly lit hallways, each of the 31 rooms and suites hides behind a black curtain, which is pulled aside for the duration of your stay. Inside, sleek furniture, soft carpets, and concrete walls contrast with white marble bathrooms, creating an altogether futuristic feeling. In fact, guests can even control the lights and sound from bed via panels in the headboard or steam their home media directly to the TV and speakers. If you need a break from all the technology, many rooms also include private balconies or terraces.

    Herman K comes courtesy of Brøchner Hotels (Denmark’s leading boutique hotel chain) and features many of the company’s signature amenities, including a healthy, organic breakfast and a “night cap hour” with complimentary drinks. Should guests want something more substantial, Herman K is also home to Roxie, a three-story restaurant from the team behind two-Michelin-starred Nordic restaurant Kadeau.
  • An Art Deco landmark on Rio’s famous stretch of sand, the Belmond Copacabana Palace has set the standard for visiting celebrities and discerning guests for nearly a century. In the luxurious rooms, muted colors, original artwork, and botanical murals serve as the backdrop for views of the ocean and black-and-white boardwalk. Outdoors, guests can lounge around the almost Olympic-sized pool—much like Marilyn Monroe once did—or take advantage of the hotel’s beach service, complete with assistants to watch your belongings while you swim. Visitors also have access to the hotel spa, which uses Brazilian fruits and Amazonian ingredients in its treatments, as well as an impeccable concierge team, which can arrange exclusive sunrise visits to Christ the Redeemer before it opens to the public.

    The restaurant and nightlife scene may be hotter in Ipanema these days but Belmond guests are spoilt for dining choices. Hotel Cipriani Restaurant—named for the Copacabana’s sister hotel in Venice—serves elegant Northern Italian, while Pérgula is bustling day and night thanks to caipirinha cocktails prepared tableside and a menu of Carioca favorites like grilled seafood and steaks. For an award-winning meal, there’s also Mee, which holds a Michelin star for its haute Pan-Asian dishes and extensive sake selection.
  • Calle de Mejía Lequerica, 8, Madrid
    It’s not that newer is necessarily better—Antonio Obrador, the hotelier and designer of famously luxurious retreats like Mallorca’s Cap Rocat, would hardly choose a neoclassical, turn-of-the-century palacio for his latest project, were that the case—but when a hotel gets the kind of buzz that the Urso Hotel & Spa got when it opened in the fall of 2014, there’s usually a reason.

    In the hip, up-and-coming Salesas neighborhood, across the street from the recently reopened (and equally lively) Barceló food market, Madrid’s first five-star boutique hotel looks, from the outside, like many grandes dames: ornate, decadent, and just a bit over-the-top. Inside is another story; while many of the original details (hand-painted azulejo tiles, grand marble staircase, stained-glass windows, windowed wooden elevator) have been painstakingly restored with the help of local craftsmen, the style is undeniably contemporary, with even a hint of Scandinavian-inspired minimalism to offset the pull of the antique. This devotion to design alone would have merited the aforementioned buzz, but Obrador and his team didn’t stop there, throwing in one of Madrid’s most innovative restaurants, most soothing spas, most understatedly cool bars, and, of course, the superlative service required of any five-star stay.
  • Rambutan Ln, Krong Siem Reap 17259, Cambodia
    Dutchman Dirk de Graaff left a demanding consulting position in Hong Kong to become a hotelier in Siem Reap, falling for Cambodia’s natural beauty, smiling residents, and laid-back way of life. He ran the first gay-friendly guesthouse in town before opening two hotels, a boutique hotel and the more upscale Rambutan Resort, a 16-room property, where he’s successfully re-created the traits that led him to the country in the first place. The simple but stylish rooms employ local, natural materials, with custom-made, chocolate-brown and white-flecked sugar-palm beds (of eco-friendly wood), brightly hued silk lamps, and private outdoor terrazzo soaking tubs. Modern Asian art—including comical pieces by Chinese artist Yue Minjun—adorns the walls. A lovely slate-and-stone tiled, tree-shaded pool anchors the property, its cascading water feature lending a meditative quality.

    And though Rambutan’s flair is more than enough reason to stay, it’s the exceedingly personable staff that makes it a true standout. Guests are welcomed like old friends (many are on return visits); the affable check-in crew and servers artfully walk the line between doing their jobs and making time for a chat. De Graaff invests in his team—providing scholarships to further their careers in hospitality, for instance—and their mutual affection for the place shows.
  • Five Islands Village, St John's, Antigua & Barbuda
    My first night at Galley Bay, I decided to take in their signature dining experience at Ismay’s. This is their top-of-the-line restaurant. Menu items include baked escalope of mahi mahi with olive and pine nut crust parsley; roasted cherry tomatoes, chilled caponata, sweet potato wafers, and balsamic reduction; and gratin of shrimp, crimson grapes, fresh dill, and champagne cream. Certainly impressive names, but perhaps the most impressive is the name of the restaurant itself. You see, when the then unnamed restaurant was being built in 2008, employees overwhelmingly suggested it should be named after one of their own: Ms. Ismay Mason. Ismay had been with Galley Bay for 45 years at that time during which she’d never called in sick and was a steadfast member of the team and community at large. Five years later, when Ismay finally retired, the tribute to her contribution toward the exceptional vibe of Galley Bay continued with the formation of The Ismay’s Foundation which provides for further career training and education within the community. Incidentally, I had the grilled beef mignon and sauté of shrimp, fondant potato, lemon, parsley and white wine emulsion.
  • 333 Franklin St, Buffalo, NY 14202, USA
    Located in Buffalo’s booming Theatre District, Buffalo Proper is a great place to stop before or after a show. Guests can look forward to nearly 30 specialty cocktails, plus seasoned bartenders ready to mix all the classics. Favorites include the BFLO Bramble (vodka, blackberries, mint, lemon) and the Bare Knuckle Boxer (whiskey, lemon, honey, and strawberry), but there’s also beer and wine should cocktails not be your thing. While the two-story, lofted space is massive, it fills up quickly on weekends, so go early to secure your spot at the bar or one of the high-top tables. Then, put in an order for your favorite drink, along with elevated bar fare like Japanese-style fried chicken, white bean burgers, and grits with crème fraîche and cheddar.