Top Travel Trends for 2019

By Liza Weisstuch
October 3, 2018
Interview on stage with screen in background
Matt Mateiescu
From advancements in technology to changes in online booking websites, the travel industry is in a constant state of motion. We got the inside scoop from industry leaders to help you keep up.

Turns out, you can learn everything there is to know about the travel industry in a day and a half. Each year, hundreds of travel executives and professionals gather at the Skift Forum in Manhattan for two days of talks that essentially comprise a state-of-the-union-like overview on the travel industry. This September, presidents, CEOs, and other head honchos of companies like Delta, JetBlue, Hilton, Marriott, and Google took to the stage to give the rundown on what’s going on with their companies and what the future might bring. While jargony buzzwords like "digital engagement" and "aligning with partners" were tossed around with abandon, there were a few key points that you, dear reader, can put in your back pocket to stay ahead of the game and think about as you plan your travel in the coming year.

THE TECH BACKLASH

After several years of news headlines and water cooler talk of Jetsonian touches in hotel rooms, some executive are tugging on the reins and bringing things back down to earth. It's a reaction that was perhaps best summed up by Matthew Upchurch, chairman and CEO of Virtuoso, a digital network of luxury travel advisors, when he said "I don’t like the term 'intermediaries.' As technology gets more ubiquitous, there will not only be a desire, but a craving for authenticity." The emotional impact of good service or a memorable interaction, he said, lasts much longer than the novelty of any gadget.

Technological enhancements in hotels, of course, cannot evolve or be implemented faster than those in society overall. Arne Sorenson, President and CEO of Marriott International, which, after the acquisition of Starwood Hotels in 2016 for $13 billion, encompasses 30 brands and 6700 hotels around the world, says there is a future for connected "smart" rooms, but we have a way to go. 

“There’s a potential for connected rooms and voice search, but it’s a tool we’re collectively figuring out how to use," he said, noting a big pilot they're working on with Amazon Alexa. "It offers convenience to do things online and through voice, but as a society we’re still figuring out: are these devices that we can trust? Does it offer enough convenience that we can be confident that it’s not listening to us when we don’t want to?”

But really, isn’t automation and digitization something people travel to escape from?After all, going on vacation to “unplug” is certainly something we all can dream about. “At the end of the day, it’s all about people. We can’t let technology override that," Sorensen added. "Everything we do is within the quest of serving guests in more effective ways, whether at our properties or online. 'Technology bling' is cool, it’s fancy, but at the end of the day, it might not work well, it may not be intuitive."

ONE-STOP TRIP PLANNING

If things go according to plan, the days of hopping from website to website to organize a trip will soon be a thing of the past. Several giant companies are expanding their offerings, aiming to become one-stop shops for an increasingly broad range of services and tools.

TripAdvisor, which is home to more than 661 million reviews of 7.7 million airlines, restaurants, accommodations and experiences, announced in early September that they are overhauling their site to include features like a social-media-like personal travel feed that includes tips, recommendations, and photos from people in a user’s network as well as TripAdvisor-appointed influencers. Users will also be able to filter their searches by destinations to find site-specific information and more comprehensive planning tools. At the conference, the company’s CEO, Steve Kaufer, elaborated, “When we look at how we make travel decisions, reviews are never the only source of information,” he said, referring to the site’s defining feature. “Everyone reaches out to friends, their social network, old-style branded content, social influencers. I envision a day when people go to TripAdvisor for the whole trip. They can save things really want and make a bucket list, of sorts. A large percentage of our audience is already Facebook-connected. People are interested in where friends have gone and what they like, we’re just streamlining that process.” 

AirB&B is also expanding its reach. The decade-old company, which has logged 400 million guest arrivals, is looking beyond accommodations at how to bring experiences into the fold. “Airbnb started with a community. There are lots of passionate artists and activities in local communities,” said Greg Greeley, President of Homes for Airbnb. “The way we think about evolution and extensions is by listening to the community. We ask: are we driving innovative travel that’s people-powered and centered on local experience?”

ON FOOD AND DESIGN

“A lack of innovation means a lack of charm,” said Ian Schrager, the legendary 1970s nightlife mogul who founded Studio 54 and later the trend-setting hotelier who pioneered the boutique hotel concept. While Schrager did not completely dismiss technology, conceding that it’s the “next frontier,” he lamented how young people don’t go to bars the way they did in the Studio 54 era and said, point blank, we’re not using technology well. It’s not about having an iPad or Echo in every room, he said. It should be more integrated. It’s about making every transaction in a hotel easier and cheaper for a reason. 

What does have an immediate and emotional impact, which ends up making a lasting impression, is design. “What takes away from personal contact is ridiculous. It's fun to razzle-dazzle customers, but attention to design has the upside to blow people away.” According to Marriott's Sorenson, design and dining are two ways to ensure that guests have a localized experience. “The product and service experience at each individual hotel has to be very strong, especially when it comes to localized architecture, food, beverage and service experience, and a team with an authentic welcome,” he said. “Fundamentally that’s the product being sold.”

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5 Things To Do in Fairbanks, Alaska

When I visited Fairbanks in early August (2018), the Blockbuster Video store was closing. It was the second-to-last outlet of the once-ubiquitous video rental depot, and it survived here because residents’ cable signals weren’t consistently dependable and, because of the town's secluded location in Alaska’s interior, internet fees have long been quite high. Technology has helped with the signal issue, but Fairbanks (population around 32,500) will always be quite isolated: Denali, a six-million-acre national park and preserve, and the 2,525,512-acre Yukon-Charley Rivers Preserve are some of its nearest neighbors. That remoteness makes the city a bustling tourist destination when it comes to viewing astrological wonders. From mid-August to mid-April, the Aurora Borealis puts on its annual show, and the midnight sun season delivers 24 hours of daylight for 70 days (May 17 to July 27). Plus, what it lacks in proximity to other cities it makes up for with a vibrant creative culture. From its time as a territory through the boom years of the Gold Rush and the oil bonanza, Alaska has possessed a mythical allure, and people have been drawn to the possibilities that go hand-in-hand with the state's sprawling landscape. Here are just a few ways that imaginative and resourceful locals take advantage of all that opportunity today, making Fairbanks an alluring American city. 1. VISIT THE MARKET (@tananavalleyfarmersmarket/Instagram) Creativity is often a consequence of living in extreme weather, especially in a remote locale. (Consider, for instance, Reykjavik, Iceland, where children are required to start learning an instrument in school at a very young age. The dark winters give them lots of time to practice, after all. As a result, the city’s lively music scene makes it a hotspot on the global map.) Fairbanks’s artists and makers are diverse and prolific, and their wares are on display at the seasonal Tanana Valley Farmers’ Market. On an impossibly hot August afternoon, as locals queued up at food stalls for crepes, Thai food, reindeer dogs, and soup, I browsed displays of handmade knives handmade by Native artisans, bowls, dishes and cups carved and whittled down from raw wood, ceramics, and knitted accessories made by a soft-spoken elderly woman named Joan who was skillfully creating new inventory as we chatted. Paintings, photographs, soaps, jams, and t-shirts were also in the mix. But about the market’s namesake farmers. Given the brutal winters, it's easy to assume that Fairbanks is barren, but the 24-hours of sunlight and warm summers make it a prime growing region. Kale, asparagus, carrots and jumbo cabbage are just a few of the items for sale. 2. FEAST LIKE THE PIONEERS There are restaurants and there are dining events. The Salmon Bake and all-you-can-eat affair, is among the latter. The location sits adjacent to Pioneer Park, frontier-themed grounds built in 1990 to commemorate the 100th anniversary of the purchase of Alaska from Russia. It includes a mock gold-rush village and a theater that stages nightly revues. The all-you-can-eat restaurant—virtually a campus—encompasses several log-cabin-like buildings that house the different food and drink stops, like the salad bar, a cute dessert bar, the spacious dining room and bar, and more, most adorned with Arctic-kitsch décor (see: colorful fake fish mounted on the walls). But the main attraction of the meal, is the grill, where a crew of personable pitmen—many of whom return season after season—turns out salmons, sirloins, and beer-battered cod, at a steady clip. They serve about 60,000 pounds of prime rib and 40,000 pounds of salmon in a season. It’s a family-run operation founded in 1979 by owner Beth Richard’s father Rick Winther, who wanted to bring fresh seafood to the interior. The beer-battered cod, in fact, is her grandmother’s recipe and is said to have been served to President Warren Harding on his 1923 trip to Alaska. Beth’s son Max, who turned 20 the day I met them, dons a grilling apron and gets to work during his summers home from college. He says his favorite offering is the homemade mousse, which happens to be Beth’s recipe. Looks like her legacy is safe and sound. 3. ENJOY COFFEE AND COMMUNITY (@venuefairbanks/Instagram) Venue looks like your average hip coffee shop, complete with minimalist furniture and art on the walls. But when Isaac Mangum, a graphic designer and native son, opened Venue in downtown Fairbanks in June 2015, he intended it to be much more than a go-to for a quick caffeine kick. “It’s where Fairbanks happens,” he told me. “Coffee is just a catalyst. You’re surrounded by beautiful things here.” To be sure, there’s a gallery-like feel to the space as well as the adjacent shop that stocks Alaskan-made goods, making it a cozy spot for locals to gather and for visitors to get a sense of the town’s easy-going vibe. And cozy is exactly what a city that endures brutal weather conditions needs. Well, that and great coffee. And there’s no shortage of spots to grab a great fantastic cup. Like many other Alaskan cities, coffee huts are abundant here. The modest roadside huts, often with cute names like Mocha Moose, offer all the artisanal espresso drinks you’d find at any full-size coffee shop. In the summer they’re a convenience. In the winter, they’re a necessity. But when it comes to hanging out, check out Lulu's Bread and Bagels, a local favorite known for fresh-baked breads and pastries. Alaska Coffee Roasting Co. and Petunia’s (now closed 2021) are also excellent choices for whiling away the hours. 4. EXPLORE THE ART OF THE AUTOMOBILE (Liza Weisstuch) Transportation ranks pretty high among the many challenges to surviving in Fairbanks’s Arctic weather. It’s not unusual for temps to fall to 60 degrees below, Fahrenheit, and lower. Given that frigidity and snow, plus the state’s massive area (it’s twice the size of Texas) and the inaccessibility of so many towns, one out of 78 Alaskans has a pilot’s license to operate small aircrafts. But before aviation was a norm, people had to get creative to devise ways to navigate snowy, icy roads. The ingenuity of engineers is on display at the Fountainhead Antique Car Museum. Among the dozens of vehicles, there’s a T-Model Ford affixed with wood runners, the creator of which christened it a “snowmobile” and patented a DIY kit, and all sorts of industrial-looking vehicles. Collectively, it’s a chronicle of how the area came to be accessible and livable. But the packed museum explores the style aspect of transportation as well functionality. Early and very rare Cadillacs and Chryslers are presented alongside the fashionable clothing of their times, which gives you a thorough understanding of what the town streets must have looked like. 5. DRINK IT IN (Liza Weisstuch) The Old City Hall in Fairbanks, which was built in 1935, sits on the National Register of Historic Places. Patrick Levy bought the building in 2014, built a steam-powered distillery inside it, started making vodka with Yukon potatoes, and christened the spirit 68 Below in honor of the freezing temps. He turned part of the town hall into a tasting room that handily serves as a local hangout and now cocktails made with the house vodka flow. Pat’s likeness to Santa Claus is rather striking, not least because the town of North Pole is 15 miles away. He delights in pointing out the irony of making booze in the same building that the town drunk tank once stood. The Fairbanks Distilling Company is just one of several spots that have a social aspect to its booze business. Brewers are in on the game, too. At HooDoo Brewing Co. you can buy your pint or a flight at the bar and drink it on the spacious family-friendly patio—in the warmer months, at least. There’s plenty of hangout space in the taproom for when the chill comes. At Silver Gulch Brewing and Bottling, the beers are served in a dim, cozy dining room with stone walls and a long wood bar. Anything from the menu of familiar comfort food makes a fine accompaniment to one of the small batch brews.For more information on Fairbanks visit Explore Fairbanks.

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5 Things to Do in Pasadena, CA

Long overshadowed by the big-city sprawl of Los Angeles and known primarily for the Tournament of Roses, Pasadena is finally coming into its own. With world-class arts institutions, an array of delicious places to eat and drink, and a splash of Hollywood-adjacent glamour, it's an ideal urban escape for Angelenos—and everyone else, too. Here's how to make the most of your time on the ground.  1. GET OUTSIDE An arbor-covered path leads from the Huntington's Japanese garden to its rose garden, where more than 1,200 cultivars of the petaled plants are on display. (Maya Stanton) It’s rare to find something that appeals to indoor and outdoor types alike, but thanks to an extensive collection of European and American art, a research library filled with treasures, and lush botanical gardens spanning 120-some acres, The Huntington Library, Art Collections, and Botanical Gardens (huntington.org) does just that. Get here early to explore the premises, from the Garden of Flowering Fragrance, an oasis in the tradition of Suzhou, China’s scholar gardens, to a walled Zen garden to one of the world’s largest collections of mature cacti and succulents. Then check out the library: Book lovers will drool over a handwritten draft of Jack London’s White Fang, a breathtakingly illustrated Canterbury Tales manuscript, and a vellum copy of the Gutenberg bible, just one of 12 known copies in existence. At $29 for adults, $24 for seniors and full-time students, and $13 for kids ages 4-11, weekend tickets are on the pricey side, but you'll need a solid amount of time here to take it all in anyway, so you'll easily get your money’s worth. Or you can just book in advance for free entry on the first Thursday of the month. 2. ABSORB SOME ART From Rodin's The Thinker to Aristide Maillol's Mountain (above) to a circa-1100 Buddha from India's Tamil Nadu state, the Norton Simon Museum's sculpture garden features work from a variety of artists. (Maya Stanton) With a lush sculpture garden, an impressive selection of 19th and 20th-century art, and a deep array of paintings, bronzes, woodblock prints, and stone sculpture from South and Southeast Asia, the Norton Simon Museum (nortonsimon.org) is as refreshing as a blast of cool air on a hot summer day. Situated on almost eight acres of land in the center of town, this jewel of an institution was renovated in 1999 by Frank Gehry and landscape architect Nancy Goslee Power, and its tranquil grounds draw inspiration from Monet’s Impressionist gardens, while its galleries provide a respite from the California sun. Come for classic work from Renoir, Degas, and Van Gogh, stay for pieces by modern masters like Picasso, Rivera, and Kandinsky, and don't miss the huge, eye-catching murals by northern California native Sam Francis. Admission is $15 for adults, $12 for seniors, and free for kids under 18 and students and military personnel with a valid ID, but those on a budget should drop by on the first Friday of the month, when it’s a free-for-all from 5:00 to 8:00 p.m.  3. EAT YOUR HEART OUT For plant-based fare, the Pasadena branch of local mini-chain Sage Vegan Bistro is where it's at. (Maya Stanton) Boasting 500 restaurants within its city limits, Pasadena offers no shortage of dining options—and, from the birthplace of culinary legend Julia Child, you’d expect nothing less. Hit Lunasia Dim Sum House (lunasiadimsumhouse.com) for extra-large, translucent har gow, baby bok choy simmered in fish broth, or scallop-topped squid-ink-skinned dumplings. In Old Pasadena, Café Santorini (cafesantorini.com) draws crowds for its stellar Mediterranean fare, from overflowing mezze plates and pastas to and oversized salads topped with generous portions of chicken milanese or lemony sautéed seafood. Just across the alley, the plant-based Sage Vegan Bistro (sageveganbistro.com) makes comfort food feel virtuous. Go light with a green juice, or all-out with avocado toast, polenta tots, or a colorful, hearty breakfast bowl. For a real knockout, splurge at Union Restaurant (unionpasadena.com), an intimate neighborhood spot that puts a California spin on northern Italian cuisine. You could make a meal out of the appetizers—a simple arugula salad showered with Pecorino pairs well with rich chunks of charred avocado, and the grilled octopus is the stuff of dreams, a crispy, tender tentacle plated with burnt eggplant, sweet-pepper puree, and Fresno chiles—but then you’d miss out on the rest of the outstanding seasonal menu. The key is to pace yourself: Order a glass of bubbly rosé and a snack to start, choose from plates like pappardelle with peppers and pork sugo or squid-ink pasta with lobster, Meyer lemon, and truffle butter, and settle in for the long haul.  4. GO BEHIND THE SCENES Pasadena's City Hall has made frequent appearances on screens small and large, standing in, with equal aplomb, for the police station in Beverly Hills Cop II and an American embassy in Mexico in The Net. Fans of Parks and Recreation might also recognize it as small-town Pawnee’s city hall. (Maya Stanton)  A go-to filming location for the likes of Rob Reiner and Quentin Tarantino, Pasadena is basically Hollywood East, and you can follow in your favorite directors’ footsteps, courtesy of a Pasadena Film Tour ($50; myvalleypass.com). The three-hour bus excursion is led by the enthusiastic Jared Cowan, a writer, production buff, and Philly transplant who’s scouted some of the city’s most noteworthy locations, from the famous facade of Doc Brown’s house in Back to the Future (a National Historic Landmark that's now owned by the city and operated by the USC School of Architecture for docent-led tours and events) to the historic Raymond Theatre, which served as the backdrop for talents as diametrically opposed as Whitney Houston and Spinal Tap, as well as less-recognizable spots like the narrow alley through which Bruce Willis escapes after his ill-fated boxing match in Pulp Fiction. You’ll never watch your favorite flicks the same way again. 5. SMELL THE ROSES Perhaps Pasadena’s best-known draw, the Rose Bowl is one of the country’s preeminent venues, and if you have a chance to attend an event here, go! Since its first college football game kicked off in 1923, the historic blue-grass field has hosted everything from Olympic events to LA Galaxy soccer games to artists like Pink Floyd and Beyoncé, not to mention 90-plus years of college football games. It more than lives up to its reputation as a great place to see a show.  THE DETAILS East of Los Angeles, some 30 miles from the airport, Pasadena is easily accessible from LAX by cab, shuttle bus, or metro. The city is highly walkable, but it also has a strong public transit system and a plethora of Uber and Lyft drivers on call at any given time. The Hilton Pasadena (hilton.com) is centrally located, just steps from Colorado Boulevard’s shops and restaurants, a 20-minute walk to Old Pasadena, and less than 10 minutes by car to the Huntington Library and the Norton Simon Museum. And, with minimal rainfall and average temperatures hovering anywhere between the low 90s in August and the high 60s in winter, there’s never a bad time to visit.

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5 Things You Should Know About Fallingwater

An open floor plan. Built-in storage. Clean, organic lines, and a harmonious indoor-outdoor balance. These hallmarks of mid-century modern design tend to be associated with American architecture in the 1940s, ‘50s, and '60s—the actual mid-century—but the style took root well before that. One of the most iconic examples of the genre is Fallingwater, a Frank Lloyd Wright masterpiece in rural southwestern Pennsylvania, built in the ‘30s, that puts an organic spin on stark mid-century simplicity. Just over an hour’s drive from Pittsburgh, the last 20 miles or so via a stretch of curvy, tree-lined, two-lane state highway, the home isn’t visible from the road; guests park in a lot and check in at the visitors’ center for the guided tour, the only way to set foot inside this storied property.  It’s a short walk from there to the house itself, and when it finally comes into view, it's hard to believe it went up some 80 years ago, thanks to its ultra-modern handling of space and forward-thinking design touches. Arguably the pinnacle of Wright's influential career, the home was designed as a weekend retreat for the Kaufmann family, department-store moguls from Pittsburgh who hosted such luminaries as Albert Einstein, Diego Rivera, and Frida Kahlo in their splendid new digs. In 1963, Fallingwater was deeded to the Western Pennsylvania Conservancy, and it opened to the public the year after. Since that time, more than 5 million visitors have passed through to pay homage to the fruits of a visionary’s labor. You'll have to book a tour to really experience this quintessential piece of American architecture, but here’s a sneak peek of what awaits behind the falls. 1. MAKING A MASTERPIECE (Courtesy Western Pennsylvania Conservancy) When Fallingwater was conceptualized in 1935, Wright was nearing 70 and in a bit of a lull career-wise, thanks to some personal scandals that made him untouchable among the upper crust he relied on for commissions. Some 30 years prior, in his early work in the Midwest, he had embraced the philosophy of organic architecture, and the Kaufmanns’ weekend retreat would turn out to be one of the most striking examples of his approach. Contrary to the family’s expectations of a home overlooking the falls, Wright told his clients that they’d appreciate it more if the waterfall became a part of their everyday life—and if they had to travel to take in the view—so he opted to incorporate the rushing water and natural landscape into the very build.  He cantilevered the entire building over the falls, making the water the focal point, its sound a constant companion and source of ambiance. The wealthy Kaufmanns agreed to pay $30,000 for a main house and a guest house, both fully furnished. ($4,000 was the average cost of a three-bedroom/one-bath home at the time.) They owned the land, and the materials were on site, so they expected that to be the end of discussion, but the final tally spiraled to $155,000—the equivalent of nearly $3 million today. But it proved worth it. The family moved in in December 1937, and Fallingwater became an immediate sensation, starring in a Museum of Modern Art exhibit and features in Time, Life, and Architectural Forum the next month. 2. PLAYING WITH PERCEPTION (Christopher Little/Courtesy Western Pennsylvania Conservancy) After butting heads with the Kaufmanns over his proposed vision and the costs it would entail, Wright began building in 1936, with concrete, native Pottsville sandstone, glass, steel and other materials excavated on site and brought in by draft horses and rail. With the idea of compression of space in mind, he created the entrance as a tunnel so visitors would approach the house from the front. You squeeze through that shadowy passageway to get inside, and when you reach the main room, it practically explodes with natural light, made to seem even brighter thanks to the preceding darkness. Wright relied on that sense of compression throughout the house to manipulate the experience, and you'll notice the contrast between darkness and light, open spaces and tight ones, as you move between the cave-like interiors and the broad outdoor terraces and walkways. Frank Lloyd Wright is widely recognized as the father of the open floor plan, a lynchpin of the Prairie school of architecture he pioneered in the early 20th century, and even as late as the ‘30s, Fallingwater’s open layout was a surprising deviation from the norm.  3. HOME IS WHERE THE HEARTH IS (Christopher Little/Courtesy Western Pennsylvania Conservancy) Wright believed that the fireplace was the centerpiece of the home, and Fallingwater is no exception. In keeping with the architect's commitment to organic materials and design, the hearth here springs directly from the natural setting. Wright fit the house into and around the boulders surrounding the waterfall on which it’s perched, and one boulder is even weight-bearing and built into the decor. It's a huge piece of rock: Half is in the kitchen, and the other extends into the living room from the outside, creating the hearthstone itself. Under foot, the floors are boulders treated with wax to make them look wet, shiny, and reminiscent of the water. 4. WINDOWS ON THE WORLD (Christopher Little/Courtesy Western Pennsylvania Conservancy) If the moving water is the star, the windows take the award for best supporting player. With steel sashes that practically float into the the walls and no blinds or curtains to distract from the view, the soaring windows welcome the outside in. (And if Wright had had his way, they would’ve been even more welcoming; for aesthetic purposes, the architect argued against installing mosquito screens, but the Kaufmanns drew the line at that.) On their own, the banks of windows are dramatic, but the understated details are just as impressive, if not more so. Take, for example, the corner windows: An innovation of Wright’s own making, the bevel-edged panes open up entirely, bringing in light where it hadn’t been before. It was a groundbreaking design element that would, in the following years, become popular worldwide.  5. THE DETAILS Nothing in the house is behind glass or protected in any way, so there’s a strict no-touching rule in effect. Guided tours are offered daily from 10:00 a.m. to 4 p.m. (closed Wednesdays); tickets start at $30 for adults and $18 for kids ages 6-12. Advance bookings are strongly recommended, and children under the age of 6 are not permitted. Admission includes access to the grounds as well as a small gallery adjacent to the visitors' center, with exhibits that put Fallingwater in the greater context of Wright's work and the Kaufmann family's background; there's also an extensive gift shop worth browsing as you wait for your group's number to be called. And, for a light bite before or after your tour, there's a surprisingly good café on site. Sandwiches and salads are prepared with more care than you'd expect, but the desserts steal the show. If it's available, definitely grab a slice of Wright's traditional birthday treat, a lighter-than-it-sounds layer cake with strawberry jam and copious-yet-ethereal tiers of whipped cream. fallingwater.org.

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6 Oahu Hikes That Belong on Your Bucket List

From picturesque views of turquoise water to stunning waterfalls and lush tropical forests, there is a trail on Oahu to please every type of outdoor enthusiast and hikers of all skill levels. The best part? Working them into a day full of other adventures is a cinch. All quadrants of the island have a hike to offer tourists and locals alike, as well as sights to see and food to devour. Whether it is a quick sweat session followed by some fun in the sun or a longer, more strenuous workout with pupus to punctuate the day, there is something for everyone on the beautiful Hawaiian island of Oahu.  1. Koko Head Crater Trail (Gennadiyp/Dreamstime) Koko Head Crater Trail, one of the most strenuous island hikes, is a former railway turned hike that is not for the faint of heart. Comprised of over 1,000 railway ties arranged like stairs, this 1.5-mile roundtrip trek will test the endurance of even the most avid hikers with steep inclines and a portion that acts as a bridge, as the under footing has completely eroded. The panoramic views of Hanauma Bay, Hawaii Kai, and Makapu’u make this hike worth it. The wide “stairs” offer plenty of space to step off to the side for a water break and it’s not uncommon to see children and runners frequenting this trail—it’s popular! Try to get here before it gets too hot, and be sure to pack plenty of water. When finished, head into Kaimuki, a suburb of Honolulu, for brunch at Koko Head Cafe (headed up by Top Chef alum Lee Ann Wong) and stay awhile to browse at Sugarcane Shop, a local boutique that sources gifts and souvenirs from local artists. 2. Lanikai Pillboxes (Kalai80/Dreamstime) Located on the east side of Oahu, Lanikai Pillboxes is a short hike that offers screensaver-worthy views of turquoise water and white sandy beaches throughout. The one-mile roundtrip trail starts with a steep vertical incline, then hits relatively flat terrain followed by a hilly peak before reaching the summit marked by two "pillboxes" (former military bunkers). Views at the top extend over Kailua and Lanikai Beaches, some of the best the windward side of Oahu has to offer, with the Mokulua Islands dotting the backdrop. Because the entrance to this hike is buried within a residential neighborhood across from the Mid Pacific Country Club, parking can be tricky, so adhere to the no-parking signs and be respectful of homeowners' driveways. The Pillboxes put you in a prime location for venturing into Kailua Town for post-hike light bites at the Kalapawai Café (be sure to order the browned-butter salted chocolate chip cookie for later), followed by shave ice, a Hawaiian staple, at President Obama’s favorite haunt, Island Snow. 3. Makapu'u Lighthouse Trail (Patrick Evans/Dreamstime) Makapu’u Lighthouse Trail’s fully paved incline makes it stroller-friendly and easy to navigate without worrying about footing, but the cliffs are steep at points, and the trail doesn’t have guardrails, so little ones have to be watched closely if they’re on their own two feet. A lookout point on the way up offers information about viewing the humpback whale migration, which occurs from November through early spring. There’s a viewing scope, but pack a pair of binoculars to increase your chances of seeing a whale or other wildlife. Views of Makapu’u Lighthouse and Koko Head greet hikers who navigate the mile to the very top, and on clear days, neighboring islands Molokai and Lanai can be visible in the distance. When you’re back at sea level, make a right out of the Makapu’u parking area, drive the coastal highway into Waimanalo for burritos at Serg’s Mexican Kitchen or a vegan plate from Ai Love Nalo, and enjoy your well-earned grub right on Waimanalo Beach, which is consistently ranked one of America’s best beaches. 4. Ehukai Pillbox Hike (Kaitlin Hanson) A short uphill hike, the Ehukai Pillbox is distinguished by the historic World War II bunkers on Oahu’s North Shore. The path’s entrance is located across the street from Sunset Beach and a muddy trail with a few built-in stairs that lead to captivating views of the famed Banzai Pipeline, where surfers like Kelly Slater and John John Florence ride the waves each winter. A painted picnic bench makes for a good water break stop before heading up to the first bunker, where the forest opens up to unobstructed ocean views. For those continuing to the second pillbox, a giant peace sign painted on a rock marks the spot where soldiers would watch for enemy ships during World War II. The incline on this 1.5-mile roundtrip hike is enough to make it slightly strenuous, so be sure to stop by Ted’s Bakery to refuel. Grab a slice of the famous haupia pie and take it across the street to eat on the sand before continuing on to explore Turtle Bay Resort, where Forgetting Sarah Marshall was filmed. 5. Aiea Loop Trail (Joshua Mcdonough/Dreamstime) The Aiea Loop Trail is an easy-to-moderate trail that clocks in at just under five miles and overlooks Honolulu and the surrounding neighborhoods. Mostly covered by lush foliage, the trail meanders through slight elevation changes and is a good choice for a more shaded experience. Part of the greater Keaiwa Heiau State Park (open daily from 7:00 a.m. to 6:45 p.m.), the Loop also leads to Kalauao Falls, which can be accessed via a side trail, an option for more experienced hikers who can easily navigate steep inclines. The trailhead is centrally located on the island, which makes it a great option before or after visiting Pearl Harbor (advance reservations recommended). On the way back toward Honolulu on Nimitz Highway, stop at La Tour Cafe for a crispy chicken sandwich, then try a coco puff, a cream-filled pastry that all the locals rave about, a half-mile down the road at Liliha Bakery. Drive just a bit further into the up-and-coming neighborhood of Kaka’ako to explore the hand-painted murals by local artists that are refreshed annually. 6. Waimea Falls Park + Botanical Garden (Kaitlin Hanson) Hikers of all levels can enjoy Waimea Falls (open daily from 9:00 a.m. to 5:00 p.m.; $17 for adults, discounted admission for seniors, children, and military), a tropical park that boasts a botanical garden and waterfall, located across the street from Waimea Bay. Around two miles out and back, the lush flora and fauna of Oahu surround a simple walking trail that leads to the 30-foot waterfall. A run-off pool below offers visitors the opportunity to cool off and take a dip under lifeguard supervision. Exhibit signs along the trail provide guests the opportunity to learn about the plants and history of Waimea Valley. After visiting the waterfall, head a half-mile up the road to snorkel or dive at Shark’s Cove, one of the best spots on the island for spotting marine life. Before heading out, walk across the street to grab a fresh poke bowl or Tsunami Sandwich from Aji Limo Food Truck, then relax on the sand to catch the sunset at Waimea Bay.