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This particular area of the Gold Coast is jokingly nicknamed the Viagra Triangle, but the Thompson Chicago doesn’t discriminate by age. The 247-room hotel is dark and moody, drawing artists of every generation to its swanky lobby bar at the back, peppered with colorful canvases and couples sneaking a snuggle in a booth. The whole town is awaiting the opening of Tavern on Rush, a reboot of the beloved steak house that used to reside just up the block. Rumors say this hangout will become a dining destination, what with its cocktail lounge, main dining room, patio, and private rooms spread across 16,000 square feet and multiple levels.


Set among all the best shopping in the Midwest, the Thompson’s midcentury-style guest rooms with hardwood floors provide the perfect minimalist location to unbox those favorite finds from Michigan Avenue around the corner. Digital nomads can book their work meetings in one of the rooms named after the Chicago Seven: countercultural anti-war protesters charged by the U.S. federal government with conspiracy and intent to incite a riot to stop the Vietnam War. The Abbie Hoffman room is a favorite.

Hailed as one of the country’s first true boutique hotels, Hotel San José started its life as a 1930s tourist court and became a 1950s roadside motel before falling into disrepair in a bad part of town. In the mid-1990s, Liz Lambert bought it and transformed it into a minimalist, mid-century–inspired hot spot, the first of her distinctive Bunkhouse hotels, and the South Congress neighborhood changed with it. Although it’s now a must-visit for out-of-town hipsters (and its bar a hangout for trendy locals), the hotel stays true to its roots; a majority of the furniture was made by local artisans from reclaimed wood and Texas leather, the three most affordable rooms have a shared bath, and Lambert’s experience renovating the hotel and contributing to the neighborhood’s gentrification prompted her to make the documentary The Last Days of the San Jose.

Nowadays, SoCo is Austin’s hottest neighborhood, and Hotel San José is in the heart of the action, hosting local and touring bands in its courtyard and parking lot, and offering some of the city’s best coffee at Jo’s, its affiliated café. Plan to spend at least one evening making new friends over Shiner Bocks at the long tables in the courtyard lounge.

Among vacationers who’ve been coming to Grand Cayman forever, there’s a whole faction that essentially camps out at Rum Point all day every day, and you’ll understand why as soon as you see the place. Tucked away, super low-key, and graced with a ridiculously photogenic pier—its perfectly weathered planks cutting a striking figure against the tranquil, turquoise surroundings—this beach is the ultimate spot for settling into a lounger or hammock between water-sports outings. Rum Point’s namesake booze—which used to wash ashore by the barrel, according to legend—is available in all manner of cocktails here, of course. But order at least one mudslide at its spiritual birthplace: the beach’s beloved Wreck Bar.

The classic cocktail list at The Rarebit is hard to beat: Moscow mules served in gorgeous copper mugs, Manhattans with a touch of Benedictine. The food menu is composed of similarly solid throwbacks: a pork chop with mac and cheese and green beans, a perfect chicken club sandwich.

Centrally located in the heart of the Cayo District, the award-winning San Ignacio Resort Hotel offers guests convenient access to the region’s best sights and activities. San Ignacio Resort Hotel features 24 rooms and has the distinction of being named “Hotel of the Year” in 2012 by the Belize Tourism Board. Room options include a honeymoon suite, regal rooms, deluxe balcony and garden rooms and one spa suite. The on-site restaurant features a number of tantalizing dishes and some of the best traditional food I’ve had in Belize. Check out the on-site Green Iguana Project and learn about San Ignacio Resort Hotel’s conservation efforts in Belize. Be sure to start at least one morning off by bird-watching over breakfast.

This perennially popular bakery and sandwich spot can feel somewhat out of place. With its cozy atmosphere in a plant-filled space, and its menu of warm panini, delicious sandwiches on artisanal breads, generous salads, and perfectly executed pastries, it is the sort of restaurant you’d expect to find in one of Montréal’s cooler neighborhoods. Instead, it’s in the heart of Old Montréal. That is a definite plus for travelers visiting the city’s historic sights. It also means, however, that there is a lunch-hour rush when nearby office workers vie for tables. If you can plan on an early or late lunch—you’re on vacation, after all—you can avoid the worst of the crowd. Olive et Gourmando is open from 9 a.m. to 5 p.m., so if you are looking for a place for dinner, the same owners are behind the new Foxy (in the Griffintown neighborhood), which is quickly proving as popular as their first restaurant.

Each evening as the sun sets, Stone Town’s Forodhani Gardens park transforms into an open-air food market. Skip the fish kebabs and head straight to the vendors selling urojo, a thick mango-and-tamarind soup served alongside chickpea fritters, boiled potatoes, cassava flakes, chutney, and as much hot sauce as you dare. Follow it up with hand-pressed sugarcane juice with ginger and lime.

A brother-sister expat duo has opened this chic slice of Brooklyn in Colonia Juárez, the neighborhood currently angling to be Mexico City’s hippest. No complaints on that account at Cicatriz, whose open, industrial-styled storefront is a forum for several daily moods. No-compromise coffee and a variety of alternative baked goods form the morning agenda; lunch means a major emphasis on locally sourced greens in great salads and roasted iterations; the meatball and fried-chicken sandwich are both major crowd-pleasers as well. After five, it’s time to get your drink on; the bartenders deliver superior, crafted quaffs, but free from all the fuss you’ll see at other haute mixology spots. The earnest, healthful menu is enhanced by an overall vibe of do-it-yourself chic.

Chef Chuck Hughes’ first flagship restaurant remains one of the best good-time spots in Old Montreal, featuring a blackboard menu full of seasonal dishes and insane cocktails. The Caesar is a must-try and comes with a salad’s worth of vegetables and a whole snow-crab leg sticking out of a monster mug. After feasting on lobster salad, short ribs with cauliflower mash, or pan-fried sea scallops with carrot butter, hang out in this dimly lit joint and watch the night turn into a party, with the drinks flowing and the music thumping louder and louder as the cooks and waiters from nearby restaurants file in after their shifts.

At Forage, a two-plus-hour tasting menu is built around trout roe, wild mountain grass, Siberian elm seed pods, and other ingredients foraged within a 500-mile radius. $87, plus $45 for wine pairings. HOW TO SCORE A TABLE: The wait for reservations is around two months. Call on a weeknight and there’s a good chance you can fill a cancellation. INSIDER TIP: This summer, cofounder Viet Pham will open a more casual restaurant called Ember and Ash that he says will “use lots of fire and a very technical, refined cooking style.” Book now. This appeared in the May 2014 issue.

Australia is world-renowned for scuba diving, but you don’t have to go all the way to the Great Barrier Reef or Ningaloo. Most people don’t know there is plenty of good diving in and around Sydney, too. One of the best sites is Magic Point off the tip of Malabar Headland National Park south of Maroubra. There’s an extensive reef system and large caves that are home to weedy sea dragons, stingrays, and a recovering colony of grey nurse sharks (which by most accounts are harmless to humans). Local outfitters such as Frog Dive Scuba Centres can lead you there.

Located in the chic, affluent area of Vitacura near Nueva Costanera, Europeo delivers a flawless fine dining experience in Santiago. The menu, overseen by executive chef Francisco Mandiola, incorporates European technique with seasonal ingredients. The dishes are perfectly seasoned and delicate. Try the spring tasting menu with dishes like tender spring vegetables with burrata cheese, or the unusual flavor combination of corn and octopus, all paired with top wines. The ambience is formal and they also put on a fabulous “executive” lunch that is very good price/quality ratio. Alonso de Cordova 2417 (between Vitacura and Nueva Costanera), Vitacura Phone: 56 (2) 2208 3603 Photo coutresy of Europeo Restaurant

Expat Dell Taylor (from New Zealand) left accounting for the restaurant business over a decade ago in Santiago when the concept of brunch did not yet exist. Café Melba was born and quickly became the place to get real french toast with real maple syrup, pancakes, eggs benedict and frothy cappuccinos. Her empire has since expanded from the El Golf locale within Las Condes (and adding alcohol to the menu for mimosas). Arrive early to get a table or be prepared to wait. Good venue for families. Don Carlos 2898, Loc 1 (Cross street El Bosque Norte) Phone: 56 (2) 2232 4546

Head outside the city centre, to the commune of Tervuren, for one of the most beautiful parks near Brussels. Just behind the Royal Museum for Central Africa (pictured here) is a large garden. Joggers and walkers frequent the network of paths through the forest and lakes are populated with fishermen on weekends. The park is home to Flanders largest Giant Redwood tree and there is a good deal of wildlife inhabiting the lake and trees. It is particularly lovely in autumn, as the leaves are changing colour, and in early spring, as the sunshine filters through the newly sprouted leaves.

This restaurant feels like you stepped back in time - think Mexico in the 70s. The story goes - it all began in the VW van in Playa del Carmen. Tacombi used to sell tacos out of the van, and now he has a nice, cozy spot in Soho where the van is parked. It’s a garage with lights strung in the air. It just feels cool to be in. The design is great, but the food is even better. Virtually any tacos you order are wonderful. I also recommend the guacamole appetizer - yum! And don’t leave without ordering a drink.