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Haleakala, a huge and dormant shield volcano, forms more than 75 percent of Maui’s landmass. As such, it pretty much demands you ascend its slopes and peer into its crater—the island’s very soul. Legend claims the demigod Maui snared the sun here, freeing it only after it swore to inch more slowly across the sky.

The 38-mile, two-and-a-half-hour drive up Haleakala climbs from sea level to 10,023 feet through several different ecological zones. One of the most popular ways to experience the volcano remains cycling down from the summit at sunrise. Do it yourself if you’re confident, or join a guided tour (Skyline Eco-Adventures offers one that includes a zip-line ride). Once you’ve mastered the motion—and the 21 switchbacks along the road—effortless downhill freewheeling rewards you with unsurpassed views of the island. If you’d rather savor the vistas from a lofty perch, drive to the top for the sunset or book an overnight at one of the park’s wilderness cabins, accessible only by hiking trail.

The real voyage of discovery consists not in seeking new landscapes, but in having new eyes. ~ Marcel Proust. For my inaugural highlight on AFAR, I am starting with my wife’s favorite quote, and a local sight in Chicago. Sometimes people feel they must jet off to some far off exotic place in order to ‘travel.’ However, if you gaze anew at your immediate surroundings with fresh eyes, you will discover an entire host of wonderful surprises. Here we have Cloud Gate, located down in Millennium Park, back before they buffed out the seams. The contrast between the organic form of ‘the bean’ and the structured grid lines, along with the warped fun house mirror quality of the city, makes this a truly unique destination.

This family-owned eatery, with its shady tables right next to the lagoon, has a delicious and affordable (under $25 per person) menu—generous, freshly prepared plates of poisson cru, garlic shrimp (a specialty), grilled mahimahi, burgers and more—that attracts guests of the nearby InterContinental Moorea Resort & Spa, who invariably return for more. Lunch only; cash only.

Even if you don’t have a train to catch, you’ll want to make time to explore all of the dining options at Denver’s Union Station. This Beaux-Arts landmark, completed in 1914, underwent a complete renovation in 2014, and now it not only serves as a modern transit hub, but houses a hotel, shops, and nearly a dozen restaurants and bars as well. Eateries include fresh seafood, oysters, and a granita bar at Stoic & Genuine; seasonally inspired comfort food at the sit-down eatery within Mercantile Dining & Provision; and locally sourced casual fare at Next Door. Pick up breakfast at Snooze, get caffeinated at Pigtrain Coffee Co., and for lunch or a quick dinner, stop by the Acme Delicatessen (and don’t forget Milkbox Ice Creamery for frozen indulgence afterward). For evening visits—postprandial or otherwise—head up to the Cooper Lounge on the mezzanine level for cocktails looking out into the station’s Great Hall.

When eating at the Sea House Restaurant, it’s hard to decide what is actually better: the view of Molokaʽi across the water, or the Molokaʽi sweet potatoes used in the frittata. Either way, both combine for a memorable breakfast on the island’s northwestern corner. Opened in 1963 when tourists were just discovering Maui, the Sea House restaurant celebrated its 50th anniversary in 2013—thereby making it one of the oldest restaurants in West Maui. Even with the history, fame, and ocean views, it’s one of the island’s most affordable restaurants. Most items on the breakfast menu will cost you $12 or less, and when you’re done with your meal, you can splash in the waters of protected Napili Bay. The Sea House sources many of their ingredients from local Hawaiian farmers (such as the Molokaʽi sweet potatoes), and they also follow traditional fishing calendars when choosing their fish for the menu. This is a great option for beginning the day on the island’s northwestern coastline and is a filling starting point for later adventures toward Honolua Bay and beyond. Or, just relax on the sands of Napili beneath the shade of a rustling palm. After all, there are only three hours between the end of breakfast and the start of the Sea House happy hour—an affordable menu that starts at 2 p.m. and has been voted one of the best on Maui.

Okay, let me start by saying that I am not trying to ignite a war with fans of In-N-Out Burger or Shake Shack. But, if you come to D.C., Five Guys is your place for burgers—we don’t go in/out or shake a shack for our bite! Yes, the burger patties at the Five Guys chain are hand-formed and cooked atop a flat top griddle. Yes, they come sandwiched between the halves of a sesame seed topped bun. Yes, you can get them in two different sizes and topped with your choice of condiments. Yes, there are some awesome fries to go with it but only fries; there are no onion rings here. You should know that Five Guys prides itself on its fries. If you want to know the type of spud that gave birth to that day’s fries, check the chalkboard for the name of the farm and location. Unless you are really, really hungry and really, really love fries, go with the small order. It’s more than what most people can devour in one sitting! For the full Five Guys experience, order your meal at the counter and while you wait, munch on the free roasted, in-shell peanuts, but don’t eat too many! You need to leave room for that awesome burger that will soon make its way to you! There are various locations around D.C. (The first Five Guys restaurant opened in 1986 here in Arlington County, Virginia.) Check the website for the one nearest you and order online to beat the line.

We all have a mental image of upscale European alpine villages from countless spy movies and Vogue fashion shoots. There’s the little café with etched glass and women sipping Alsace with perfect hair and puffy parkas. The men are capable sorts, usually lean and well-traveled. Jet-setters, rich ski bums, and other dubious types mill around low-slung Citroëns with skis on the back, while the air feels charged with intrigue and adventure simmering under the laissez-faire insouciance. Sorta like the Arrabelle at Vail Square. “There’s no other place like this in North America that captures the iconic ambience of classic Old World European cities like Salzburg, Innsbruck, and Prague,” says John Dawsey, director of sales. “During the design phase, we really wanted to capture a feeling aligned with a cultured European central plaza.” The Arrabelle consists of 86 suites overlooking the town square, which converts into a skating rink in winter at the gondola base of Vail Mountain. The charm is in the details: working wood shutters, copper drainspouts, and subtle fairy-tale stenciling around the Bavarian Biedemeier-style architecture. The lobby’s windows are Czech, no less. Off the lobby, the Tavern is always buzzing with locals and visitors in the shadows sipping hot chocolate and Grand Marnier. The menu is meat-friendly. Try the Bone-in Veal Schnitzel with saffron risotto because that’s what spies and dangerous women eat.

Pescheria Mattiucci is a fish store by day that transforms itself into a small standing-room-only restaurant a few nights of the week. Mattiucci is an old family operation, but this place is the brainchild of a young son, Luigi Mattiucci. Luigi speaks to me from behind the counter as he preps plates of fish. “There’s a tradition of eating raw fish in southern Italy,” he says. “But it wasn’t a restaurant thing. It was something fishermen did because they couldn’t store all the fish they’d caught.”

He passes me a plate of raw red shrimp with the heads still on, slices of Sicilian tuna, and some amberjack, all of it topped with only a spray of lemon juice and some thick grains of sea salt.

Mattiucci has expanded his family business, which began as an outdoor fish stall in the Quartieri Spagnoli. (Everything artisanal in Naples seems to originate from there, probably because only a poor neighborhood like that could supply the child labor that was the foundation of old-school artisanal culture.) Mattiucci expanded from that original location into this store in posh Chiaia and also bought fishing boats in Sicily so they could eliminate the middleman. He serves me a dish of baby calamari stuffed with friarelli, a distinctively Neapolitan bitter green. Then he offers me a sample of a new dish: the same seafood stuffed with sprigs of spring vegetables, just now in season. Mattiucci, I realize, is someone who’s taking an artisanal approach to the very traditional, and non-artisanal trade of fishmongering. He’s already expanded his restaurant to London and Milan, but Naples is still where he cooks himself. “The fish is freshest here,” he says.

At this intimate Marylebone hotel, there’s a unique history that goes beyond its setting in a Regency townhouse, or its location overlooking one of London’s earliest cricket grounds. Of more interest to hotel junkies is the fact that, back in 1985, this was the first hotel opened by Tim and Kit Kemp, who went on to found the much-loved Firmdale Hotels group, which now has properties throughout London and New York City. Though the couple sold Dorset Square in 2002, they re-bought it in 2012, and gave it a thorough re-do to bring it back to their signature style standard.

The 38 rooms now feature modern English décor, complete with individually selected furnishings and eye-catching fabrics, as well as Wi-Fi, iPod docking stations, and granite bathrooms with walk-in showers or bathtubs. The top-tier Marylebone Room kicks it up a notch with grey wool walls and a separate sitting room. Some of the rooms run small, but luckily there are comfy public spaces in which to hang out, including a lovely ground floor library with fireplace, honor bar, and views of the square. The Potting Shed restaurant is both a guest and local favorite for its gourmet menu and all-day afternoon tea, as well as its Chef’s Table dinners and weekend Prosecco Brunch. The team here can also put together a custom picnic hamper, stocked with eats, drinks, and a blanket for enjoying in the square or nearby Regent’s Park.

Dream about a Caribbean beach bar and chances are you’ll imagine someplace like MooMba, just south of Palm Beach. Here, you’ll find oversize palapas, tiki torches at night, and a crowd looking for fun with their feet in the sand. From its lounge chairs positioned under swaying palms to its extensive list of tropical cocktails, the watering hole is really what an island vacation is all about. To eat, there’s a buffet, with Sunday’s beach barbecue theme being your best bet. Go at happy hour, which is timed to coincide with the sunset, then stay into the evening for live music and DJs.

We had the fabulous opportunity to spend a week at the Venetian and here are my findings. I loved it the minute I got out of the taxi. It has an opulent front entrance, with a massive ceiling adorned with frescoes. Inside you are greeted with more luxury as the lobby is all marble. The front desk is extremely efficient as one would expect from a five star hotel and among best if not the best in Vegas. We got in very late and had no desire to go out to eat so we ordered room service. The menu is extensive and delicious and they offer a lot of healthy choices. The service was a bit slow but the food more than made up for it. Our suite was large and comfortable with two queen beds and a generous sitting area. My only complaint with the Venetian, as with all the casino hotels in Vegas, is that the smell of cigarette smoke is present everywhere in the main lobby and casino and you cannot avoid it as walking to most restaurants requires walking by or through the casino. Apart from that I love it.

Located on the island’s unassuming south coast, down a street that doesn’t even have a name (which isn’t uncommon in Barbados) sits a little beach bar called the Carib. Wander up to the wood deck and smile at the Bajan waitress pulling double-duty behind the Mt. Gay Rum-lined bar, as she waves her hand at you, the universal sign for “just sit anywhere.” Pull up a non-luxurious plastic chair and soon you’ll find a cold Banks in your hand (the local brew - about the color of a Bud Light but with much more flavor) and a plate of steaming Bajan food on its way. The Carib, which I eat at almost daily during my time in Barbados (I’ve been to the island seven times), has the best flying fish on the island. Order yours platter or sandwich style, with sides of cou cou (a local dish about the consistency of mashed potatoes) and salad. Be sure and start your meal with a basket of pipping hot fish cakes - also the best on the island. Luckily when you’re done with lunch and ready for a nap, the beach is a few steps away. Grab a chair and an umbrella for $10 U.S. for the entire day. You probably have the beach to yourself, until school gets out when the local youth will stop by for a dip in the ocean and maybe a game of cricket.

Ultraviolet is the kind of travel experience you talk about 10 years later. French chef Paul Pairet first dreamed of a multisensory dining adventure in 1996, but it took until May 2012 to open this transcendent restaurant. There’s room for only 10 diners to experience the 20-course meal at one time, and the dining room is a theater with HD screens for walls. With every course, the sounds, sights, and even smells change to complement and amplify the menu. The sublime sea bass Monte Carlo—sea bass with fresh mozzarella and sun-dried tomatoes inside a baguette—is served to the sound of Debussy, and as you eat you’ll notice a vibrant aquarium has appeared right in front of you.

This lovely state park stretches along the rugged volcanic shoreline of western Maui, three miles from Hana. It’s best explored on the 2.2-mile hike that starts at the black-sand beach and follows the dramatic coast, passing lava tubes, rock arches, blowholes, and Polynesia’s largest heiau (an ancient Hawaiian temple) along the way. Avoid standing too close to the geysers as well as the lava benches near the ocean, which can crumble easily, and watch out for high surf. If you’re looking to cool down after your trek, take the loop trail to the park’s freshwater caves, where you can explore two separate chambers (the first tends to be clearer and more inviting).

Bloody Mary’s, entertaining tourists since it opened in 1979, is one of those Bora Bora experiences that simply must be done. The ambience is beach-bar hip, with sand floors, colored lights, and coconut stools in a dining room under a thatched roof and surrounded by tropical foliage. Even if you don’t eat here, at least come for a cocktail to experience the vibe and mingle with the crowd of local pension, or guesthouse, owners, visiting celebrities, and other travelers. The food’s quite good, too: Fresh fish, seafood, and meats are grilled, American-barbecue style, with tasty results.