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The hot-right-now Fierro Hotel bills itself as the ‘Hotel for the Gourmand,’ and it’s no wonder - the boutique hotel is famous on the foodie scene for hosting special events like ‘One Table,’ the biweekly TFIF Happy Hour brings in the talent of celebrity bartender Fede Cuco, and - drum roll, please - resident chef Hernán Gipponi and his restaurant were recently recognized at the Latin America’s 50 Best Restaurants Awards 2013. To see what Gipponi - who honed his craft at Michelin-starred restaurants in Spain - can do, come for the nine-course modern Argentinian tasting menu, or splurge on his classy weekend brunch.

You know how they say that Montreal is a happy mixture of North America and Europe? Well, if there’s one place in the city that’s truly unique, and not influenced by any other colony, it’s Plateau Mont-Royal. Located just a few minutes north of downtown, this neighborhood is lively, colorful, and somewhat eclectic. Here young families, hipsters, and fancy folk mingle together in harmony. In this iconic area you will find everything you need—from French bistros, typical French-Canadian brunch joints, clothing stores, and fine groceries. Nothing is expensive as such, but restraint is in order, because absolutely everything is enthralling!

Blueberry Boy Bait may sound like a B-side song from an alternative band, but it’s actually just an ice cream flavor offered by Humphry Slocombe, a small shop in the Mission District. Owner and former pastry chef Jake Godby has made the name Humphry Slocombe synonymous with flavors and ingredients not often found in ice cream or sorbet. Case in point: best-seller Secret Breakfast, the flavor that launched a thousand Humphry Slocombe fans, a combo of homemade cornflakes and bourbon. Traditionalists will be happy to find “normal” flavors, too, but it’s Godby’s “march to your own drum” ethos that brings out his best work and keeps people lining up for creative scoops. Pick up a copy of The Humphry Slocombe Ice Cream Book, with 40 recipes you can re-create at home.

The Iris Inn, a luxury Shenandoah bed and breakfast, is the perfect base to explore Virginia’s Blue Ridge mountains. Located 30 minutes from Charlottesville, the Inn is close to nearly 30 wineries and is within a few minutes drive to the southern entrance of Shenandoah National Park. Owners Dave and Heidi Lanford warmly welcome visitors to their cozy mountainside inn with gourmet breakfasts and a complimentary nightly happy hour. The eco-friendly B&B also offers an electric vehicle charging station.

If you want to check out where the San Diego locals hang out, you have to stop by Bootlegger, located on the border of Gaslamp. The bar itself is unique, with a beautiful stone top and lined with hand-carved wooden panels imported from Mexico. There are comfortable seats no matter where you look. Although the decor is going for that dive bar feel, it’s got a touch of hidden elegance. When you come in, as long as it’s not too crowded, the service is highly personable. The Bootlegger is designed somewhat to look like a 1920s speakeasy, and has some interesting art on the walls. The drinks are poured using top-grade liquors; my favorite so far (pictured) is the ‘Old Fashioned'—Bulleit Bourbon, Angostura bitters, sugar, fresh lemon and orange peel. They have a good number of beers on tap and a great selection from the local micro-breweries. I recommend the happy hour—it’s not too crowded and select drinks and all appetizers are half price. For a neighborhood bar, the food is really good. The Bootlegger bar is a great place to experience the San Diego vibe. Another cool thing is that they don’t allow smoking out on the patio around the bar, so if you want to enjoy a smoke-free night, this is the place to be. Tip: It gets impossibly crowded during any game going on at Petco Park, which is the local baseball stadium. During the late week to weekend it also gets crowded. If you want to come and chill before a night on the town, come by for the happy hour, from 3–8 p.m.

The Wauwinet makes the most of its coastal setting between the Atlantic Ocean and Nantucket Bay. Next to the Coskata-Coatue Wildlife Refuge, the resort has 32 rooms, plus four cottages with separate living rooms and the three-bedroom Anchorage House across from the main inn. In addition to private beach access and bikes to explore the island, guests can take out a kayak, play a game of tennis, or watch a movie in their room with hot buttered popcorn. A spa offers sea-inspired facials, massages, and body treatments. TOPPER’S restaurant is known for its Retsyo oysters, harvested only 300 yards from the restaurant, and offers transfers to and from White Elephant Hotel’s Brant Point Grill on its 21-passenger boat, Lady Wauwinet. The inn also provides regular shuttle services to the ferry and Nantucket town (about 10 miles away), and outside of peak summer season will drive guests to the village of ‘Sconset in its 1947 Woody station wagon.

A stay at OneFortyEight, in Nairobi’s Langata suburb, feels like hunkering down at your most stylish friend’s home. The former private residence has eight eclectic rooms that blend regional artwork, custom furnishings (by local fashion designer Anna Trzebinski), gothic touches, and feminine finishes and come in a variety of layouts to satisfy every kind of traveler, from two-storey apartments to a three-bed loft perfect for children. A large, welcoming fireplace sits in the middle of the living area to greet guests, dinners take place around a giant wooden table, and a covered lounge overlooks gardens filled with grazing warthogs and tree-leaping monkeys. Days are spent visiting nearby sights—dropping in on the giraffes at the African Fund for Endangered Wildlife Center, adopting a baby elephant at the David Sheldrick Wildlife Trust, or walking in the footsteps of Karen Blixen. Of course, no one could blame you for holing up for the night: each room has access to Wi-Fi and Netflix.

Among Charleston’s two dozen thriving breweries, Revelry may have the best digs. It’s located in the peninsula’s NoMo neighborhood and sports a spacious, laid-back rooftop deck bar that’s perfect for viewing sunset over the Holy City skyline. The whole place is adorned with art—including on its cans’ labels—by recognizable local artist, Chris Kemp. Fortunately, what’s inside the cans is equally memorable. Brews like “Gullah Cream” and “Poke the Bear” (an American Pale) are among the city’s signature ales for any beer lover seeking the best of Charleston. Happy hour features live music Friday through Sunday, making Revelry a go-to gathering place.

On the ultra-exclusive island of Mustique, Basil’s Bar is a stargazer’s paradise—and not just at night. It’s a favorite of celebrities, meaning you never know just who will be seated at the next table. A series of roofs cover the open-air deck to shade diners from the hot sun and occasional shower as they enjoy tropical cocktails and freshly grilled lobster. Come for the dance party on Wednesday, the happy hour on Thursday, or the sunset jazz every Sunday at 5:30 p.m. Basil’s also hosts the Mustique Blues Festival at the end of January, with live music each night for two straight weeks.

It sounds like a Portlandia sketch: the Northwest pizza joint with an on-site chicken coop, where you can get any pie topped with a soft-cooked egg. But Humble Pie is quite serious about their pizza (and their chickens); their goal is balancing Asian and Pacific Northwest architectural elements with sustainable urban farming. That means sunny wooden picnic benches right next to the outdoor coop, and sharing a table with new friends during their busy happy hour. The menu is heavy on local and organic ingredients, including the beer and cider selection. Our favorite was the pulled pork, pickled onion, and Beecher’s mozzarella cheese pizza — with an egg on top, of course.

Liguria is an institution in Santiago. It’s the default for meeting friends and colleagues over chilled draft beers called schops, or dangerously loaded cocktails. The bar scene is animated and starts in the late afternoon around happy hour and ends in the wee hours of the morning. The kitchen pumps out tasty Chilean bistro-style fare ranging from countryside rabbit in mustard sauce to their much renowned “carne mechada,” a braised beef in tomato and red wine chopped up on pasta or sliced down into sandwiches. Get there early to score a table or make friends with the bartender. Best Locations: Metro Tobalaba on Luis Thayer Ojeda & Metro Manuel Montt (address listed here). Photo: Qantas

Part restaurant and part performance venue, the Rendezvous is a full night out in one cozy spot. The restaurant has typical bar food (burgers, salads, deep-fried snacks) that’s basic but good; happy hour goes from 3-6 pm daily with food specials. The tiny Jewelbox Theatre is an intimate cabaret-style theatre, where you’ll find everything from burlesque to comedy variety shows to live music and theater. They also have two excellent private rental rooms for parties. Upstairs, the Red Velvet Lounge looks out onto the main dining floor and has its own sound system. Downstairs, the basement-level Grotto is a dark, red-lit cave with its own private bar and plenty of room for dancing.

Voted “Best Waterpark in the Area for the Entire Family” by Chicago Parent in 2011, this water wonderland is fun for all ages. Parents can lounge around the pool, catching some rays in the sun, and the kids can romp around the Caribbean-themed park as they wish. The waterpark also offers swim lessons, birthday party packages, or the ability to rent the entire place for your own private event. And lest you or the little ones need a snack, the onsite concession stand will be more then happy to get you a little something to nibble on as you while away the hours of a summer afternoon.

Every Saturday and Sunday on Via S. Teodoro, tucked just off Circus Maximus, Rome‘s best farmer’s market takes place. It’s run by Campagna Amica, an Italy-wide organization that promotes local, sustainable agriculture—so all of the products sold here, from jam to olive oil, bread to cheese, beer to wine, come from the Lazio region only, and are sold directly by the producers themselves. Tastings are a-plenty and the producers are more than happy to chitchat about their foodstuffs. If you come around lunchtime, you can buy a cheap lunch—maybe even including porchetta sliced right off the pig, like here—to eat on the picnic tables outside.

Unicorn is one of my favorite places to take visitors because there’s just so much to look at: the lurid circus-painted walls, the costumed and accessorized taxidermy, the lavishly painted bar that seems to have been pulled off a carousel. During happy hour, load up on discounted snacks like “narwhal balls” (deep-fried potato croquettes with dipping sauce), hand-dipped corn dogs, and bacon popcorn. They recently expanded into the basement, now known as Narwhal, which has another full bar and a selection of vintage arcade and pinball games. It gets wild on weekend nights, but you can stop in on a weekday afternoon or evening for a more sedate experience if you just want to soak up the colorful surroundings.