Should You Go on Vacation with a Travel Influencer?

(Photo: Courtesy Trovatrip)

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Published: Jul 17, 2024 Updated: Jul 18, 2024

New booking sites are connecting travel influencers with their followers to take trips all over the world. But should you go? I headed to Yosemite with an influencer and her fangirls to find out.

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I was thinking about going to India with Hannah, or Bali with Ashlyn, maybe Morocco with Emily Rose. But then I came across Yosemite with Haleigh. Haleigh looked so happy. So carefree. Her arms open wide, embracing the wilderness. I, too, wanted to clasp my coffee mug while watching the sunrise and swing in a hammock slung between pines. It had been too long since I’d gone backpacking! I didn’t know Haleigh’s last name or anything about her. No matter. Haleigh made life outdoors look so easy. So perfect. On Instagram, at least.

Recently, the algorithm has been inundating me with women like Haleigh—pretty, approachable, adventurous, always on a trip somewhere lovely. And suddenly all of them seemed to be inviting me to join them. Trekking in Peru. Strutting through Parisian streets. Leaping into turquoise waters in Tahiti. “Travel with me!” their painstakingly curated feeds read, leading to links where all you had to do was click and pay, then pack a bag.

I wanted to go. Follow the followers. See what traveling with a travel influencer was all about. But India with Hannah sounded… far. Better, I thought, to stick a little closer to my home in San Francisco; drive my own getaway car. So I clicked Haleigh’s book-now button, put down a $600 deposit, and, when summer came, headed east to Yosemite, to meet up with a bunch of women I’d never met before.

Most of the dozen others had flown in. Strangers all, waiting at the airport for the sort-of stranger who’d lured them there. And then there she was, in the flesh at SFO: @, a lithe 32-year-old with a waist-length dirty-blond braid, wearing Stio pants and Chacos, walking toward a van full of her followers. And everyone was quietly freaking out.

“There was this fangirl moment,” Jeanne, a restaurateur from North Carolina, mother of four, and at 51 the eldest of our group, told me later. “No one said it out loud or anything, but you could feel it. This nervous energy. It was like: Oh, my God! There she is! She’s real.”

There’s a wide, rapidly expanding world of influencer-led trips out there, and most live on , a newish booking site that allows influencers to commune with their influenced anywhere from Croatia to Cartagena. “We’re a platform and marketplace that helps influencers and travelers connect with their communities, wherever they want to go,” says Lauren Schneider, Trova’s 35-year-old cofounder. Schneider, a former digital-advertising account executive from Portland, Oregon, launched Trova in 2019 with her friends Brandon Denham and Nick Poggi. Business was slow at first, but it started taking off post-pandemic. Schneider credits “the loneliness epidemic” among millennials and Gen Z. Social media was crucial during COVID, but “the second you close down that app, it’s lonely,” she says. “People are craving connection.” Travel helps “cure a sadness.”

Trova isn’t the only venture to see travel influencers as potential trip leaders. Camp Wanderlost, a company based in Baja California that offers pop-up and permanent glamping outposts, also offers retreats for influencers and their ilk. Its mission: “To make social media social,” as the website puts it. “It’s time to stop living vicariously through others and create our own adventures.” EF Go Ahead Tours, a 55-year-old travel company originally geared toward the over-50 set, launched a Travel Influencer Program in late 2021, plotting more than a dozen related trips over the next two years. Ultraluxe new travel companies like Paragon and Satopia are predicated on influencers of a more exclusive sort: star chefs, top-tier sommeliers, and pro athletes. Five days dining with Dominique Crenn in the French countryside ($35,000). Riding in Japan with professional snowboarder Travis Rice ($50,000). A handful of travel bloggers have also been organizing group trips on their own for several years. Alyssa Ramos, a.k.a. @mylifesatravelmovie, runs an outfitter called @mylifesatraveltribe, which offers “badass #GroupTrips for Badass People.”

TrovaTrip isn’t technically an outfitter. It’s a tech startup with $15 million in initial funding that functions as a middleman, contracting with actual travel outfitters to organize adventures hosted by influencers. Trova ran 475 trips in 2023, working with more than 340 influencers. This year, they’re projecting close to 600 trips. Associates at the 100-person company, which is also based in Portland, are constantly reaching out to a seemingly bottomless well of nano-influencers (people with four-digit follower counts but high engagement), micro-influencers (10,000 to 100,000 followers), and macro-influencers like Haleigh who have more than 100,000 followers. Haleigh says it took four emails from Trova before she responded: “I had no idea what it was.”

Here’s how it works: The influencer posts a poll asking her followers where they’d like to go. Alaska? Costa Rica? Iceland? If they get at least 50 responses, the trip is listed on Trova’s site at a price suggested by the company but finalized by the influencer. The influencer then pushes the link, inviting any and all. If she—around 85 percent of Trova’s hosts are women—gets at least eight bookings, the trip is a go. Most would-be travelers come across the trips through their Insta feeds, like I did, or the company’s marketing emails. But direct traffic to Trova’s site is increasing.

Trips are typically a week long, and the average host earns $7,500. In exchange, all the influencer has to do is show up and be nice, maybe hold a pre-trip Zoom call or lead the group through a few sunrise asanas if they want. Trova manages the details: itineraries, sign-ups, logistics, and insurance. Once the trip starts, a group of actual guides handle things like dishwashing, water purification, and, you know, survival. The host is more like a figurehead. “The community gatherer,” as Haleigh put it. “Don’t worry!” she said shortly after everyone arrived. “I’m not in charge of your safety!”

Haleigh’s trip to Yosemite, her first with Trova, cost $2,495—and sold out in a day. Becky, a 42-year-old sales director from Florida, didn’t hesitate to sign up. “I just wanted to go backpacking,” she explains. “I thought: ‘Haleigh looks like she knows what she’s doing! I’ll go with her!’ My husband was like, ‘Are you out of your fucking mind?’ ”

Haleigh made life outdoors look so easy. So perfect. On Instagram, at least.

Hours before the trip, Haleigh started to wonder if maybe she was, too. Most of these women had never backpacked before. What if it rained all week? What if they hated it? What if she hated them? What if they hated her? Worse, what if they all wanted to be her best friend? Who were her followers anyway? And, oh God, were they expecting her to be on 24/7 for six straight days? Because contrary to how she might appear on Instagram, Haleigh tells me, she actually hates social media.

She never intended to be an influencer. She also really hates being called one. Most do. “The word ‘influencer’ undermines the realness of the person on the other side,” Haleigh says. “I never set out to influence anyone!” The preferred term these days is content creator. Or, as Trova’s Schneider calls them, simply: creators.

Haleigh, whose last name is Hendrickson, started creating content in 2015, blogging on a personal website for friends and family while in the Peace Corps in the Philippines. The blog was called Where She Went Next, but then she met her future husband, Cole Hendrickson, during volunteer training, and eventually rebranded to
@wherewewentnext. Which was Oahu, where Haleigh got a job teaching sixth-grade English and was miserable. “I’d hit rock bottom,” she says. To her then 900 or so Instagram friends, she was living in paradise. But she wanted a change.

In 2019, motivation came in the form of a mass DM from a teeth-bleaching company. Fifty bucks to pimp her pearly whites? Why not? “It opened this whole new door,” Haleigh says, to a potential revenue stream she never knew existed. She googled “How to Monetize Instagram.” Watched webinars. Cold-emailed a travel blogger who goes by @bucketlistbri and asked her to be her mentor. “She was just a random woman online who was living my dream,” Haleigh says.

Her dream? To be a writer. “Of short things,” she says. She’d flirted with the idea of working on guidebooks for Lonely Planet, until she discovered, as many guidebook writers do, that the compensation wasn’t worth the slog. Maybe, Haleigh thought, if she could drum up more followers on Instagram, she could drive more readers to her blog and generate enough income from online ads to leave teaching.

By the summer of 2021, she had grown her following to about 4,000 or 5,000—just enough to feel comfortable quitting the classroom. She planned a monthlong trip to photogenic southwest Utah. “We’ll sleep in a tent the whole time!” she told Cole. Hike through slot canyons. Dunk in waterfalls. Post about it—and hope it catches on. It didn’t. “I was making all these reels about our wild adventures, doing everything right, and nothing was happening,” she says. She returned home deflated. “I thought: Well, that was fun, but it didn’t really take off.”

Until one morning a month or so later, when Haleigh woke up to 8,000 new followers. One of her Utah reels had gone viral overnight.

Suddenly, Fabletics, an athleisure brand backed by celebrities like Kate Hudson, was following her. Soon she had 30,000 followers, then 50,000. Haleigh was floored. “I just kept refreshing my page thinking something was going wrong,” she recalls. “It was the craziest day of my life!” Nike, Eddie Bauer, Columbia: brands came calling that she’d grown up wearing as a kid in small-town Kentucky. Next thing she knew, she had more than 100,000 followers, and a new job: going somewhere pretty and smiling for her own camera.

The group hanging at camp, sharing stories (Photo: Haleigh Hendrickson)

Chats around the campfire (Photo: Jordan of The Homebody Tourist)

Our adventure would be a six-day march along Yosemite’s north rim, a roughly 25-mile loop past creeks and waterfalls that started with an ass-kicking climb. We were supposed to spend the first night in the backpackers camp on the Valley floor. Alas, thanks to flooding, we’d been redirected to the Indian Flat RV Campground, a dusty parking lot off the highway, crowded with cars, kids, plastic coolers, and portable barbecues. Still, Haleigh and her harem were upbeat.

Three women from Wildland Trekking, the Flagstaff, Arizona, outfit that Trova contracted to run the trip, made fajitas for dinner. “I wish I was a guide!” Haleigh says, perhaps sensing her murky role. “They’re so cool.”

Later we laid out the contents of our packs so the guides could assess our loads. Extra underwear, bars of deodorant, journals—anything deemed unnecessary—were discarded. I fought to keep my book. Haleigh refused to give up her hammock. “It’s for everyone!” she insisted. At 5.8 ounces, it was also light enough to carry for the not insignificant price she commands to post about it.

The next morning, mere hours into our hike, 29-year-old Jordan, from Dallas, peeled off the trail and shouted, “Hey, Haleigh! Want to video my first time peeing outside?”

“Absolutely!” Haleigh cheered. I was primed. Prejudiced. I fully expected Haleigh to bust out her phone and start filming. Everything is content, right? And then I realized they were joking. I was relieved. And soon so was Jordan, who returned triumphant.

Jordan is an ex-teacher turned travel blogger, just like Haleigh. Except not exactly like Haleigh. Jordan actually hates traveling. Hence her handle:
@thehomebodytourist. Her niche is staycation-y weekend adventures. Happy with her relatively measly follower count (6,000) and monthly page views (around 30,000), she has no Haleigh-level aspirations. She only posts, she told me, because it’s a flexible way to earn an extra $1,000 or so each month, and to spend more time with her husband, a police officer who works nights. The only reason @homebodytourist left her home and traveled all this way was to check backpacking off her things-to-do-before-30 list. When she saw Haleigh’s Instagram invite, she didn’t think twice.

“Don’t worry!” she said shortly after everyone arrived. “I’m not in charge of your safety!”

Liz, a 28-year-old nurse from Chicago, was warier. She wasn’t a follower of Haleigh’s—her friend was, and had convinced her to sign up together. Then the friend bailed. Liz decided what the hell, she’d go anyway. “I was like: Who is this lady I’m trusting with my life for a week?”

As we continued our climb up Snow Creek Canyon, which gained almost 4,000 feet over 3.7 punishing miles, I fell into step with Amanda, a 24-year-old flatlander in new hiking boots and a white cotton tee. She explained that she’d been hooked by one of Haleigh’s Hawaii photos. “She was wearing this super cute rash guard on a surfboard. The water was crystal clear. And I was like, Yes! I need that in my life!”

Instead, in this moment, her life was kind of miserable. We were trudging up 108 switchbacks beneath a beating sun, lugging bear canisters and some 35 pounds each. Amanda was at the rear of the pack. And yet she was having a blast. “I look up to Haleigh,” like a big social media sister, she said. “A lot of influencers come across fake or feel pornographic, but Haleigh keeps it real. You see her photos and think: I want to be part of her friend group.”

Our crew was about as homogenous as a Bama Rush sorority in hiking boots. We were 15 straight, white, barely wrinkled women, guides included, and all but three of us had at least two tattoos and zero kids. Half were wearing the same knit Carhartt hat as Haleigh. Also, as Haleigh surmised, “I bet we’re all sevens!”—a reference to the Enneagram personality quiz. (We were, in fact, all sevens, which according to the Enneagram scorecard makes us “enthusiasts”: curious and optimistic, with a sense of adventure.) The real common denominator, though, was Haleigh. And as was obviously true by the second night, that was enough.

“Y’all mesh really well together,” said Katie, a veteran Wildland guide who was stirring a pot of chickpea pasta over a propane stove. She and the other guides admitted that they’d been skeptical. “I was wondering what the dynamic would be,” said Rachel, a quiet, 28-year-old rock climber. “Was everyone going to be, like, her fans? Are we going to be modeling and taking pictures the whole time? Turns out this is very normal.”

It isn’t always. “I ran Wildland’s first TrovaTrip, and it was a fucking hot mess,” said Katie, who typically leads Wildland’s llama treks. “Some photographer chick.” It was a power struggle, Guide versus Influencer. Personalities were loud. Roles unclear. Spotlights stolen. Tips embezzled. Katie had sworn off guiding for influencers after that. As she put it, “I’d rather hang out with llamas.”

Recently, though, word around Wildland was that the TrovaTrips had gotten better. Katie agreed to give it another go. She looked around camp—at Haleigh chatting away, at three women doing daffys, at friendships forming. “This isn’t so bad,” she said.

Excited selfies (Photo: Jordan of The Homebody Tourist)

��ϳԹ��s along the way (Photo: Jordan of The Homebody Tourist)

Influencers often talk about their “communities.” Which is really just a cozy term for commenters, likers, and DMers. Basically, a bunch of internet strangers engaged in what psychologists call a parasocial relationship: a one-sided connection a fan often feels from afar with, say, a rock star or author. Rarely, however, are these communities tested in an intimate, let’s-share-a-tent kind of way.

It made me think of one of those fifth-grade word problems. If Liz likes Haleigh, and Jordan follows Haleigh, will Jordan also like Liz? Apparently the answer was yes, because there they were: Liz and Jordan, instant besties, on Haleigh’s heels. Spontaneously bursting into a complicated choreographed handshake throughout the week and filming it in front of Yosemite Falls, along a rushing creek, atop North Dome. “I’m going to edit it when I get home,” Jordan said. “You know, so it looks like one handshake with all different backdrops.”

Before dinner I found the two of them doing an impromptu photo shoot with a puffy blue Hest camping pillow, logo on display. “I needed to buy a camping pillow anyway,” Jordan said. “So I just emailed them and asked: ‘Do you want to give me one and pay me for a post?’ ” The company sent her a pillow and $300.

Going on an organized group trip because you admire the person leading it is nothing new, of course. Yoga students join their gurus in Costa Rica. Writers go on retreats with bestselling authors in Big Sur. You can cast lines with famed YouTube fishermen, eat your way through Italy with revered chefs, and trek with TikTok comedians. What all these hosts have, though, is something many ordinary influencers do not: a talent, an obvious area of expertise that makes following them across the world make sense. Whereas travel influencers just, well, travel.

The influencer-marketing industry is expected to grow to $24 billion by the end of 2024. According to a 2021 poll conducted by social media marketing firm SocialStar, 84 percent of millennials and Gen Z said they “usually use travel influencers for recommendations.” A 2022 survey from the Pew Research Center found that 53 percent of those who follow influencers say they’ve purchased something after seeing an influencer post about it. Hotels and ski resorts, tourism bureaus and hospitality brands, and cruise lines and glamp grounds now list “influencer collaboration requests” above “media inquiries” on their websites. They are bombarded daily by one-woman brands requesting freebies in exchange for their reach.

Marketing departments of all sizes connect with an infinite scroll of influencers. Last year the small-town tourism agency Visit Bend spent $134,000 on them, which generated more than $10 million from visitors: a 7,000 percent ROI. “Didn’t Haleigh Hendrickson @wherewewentnext do some stuff for you?” I asked when I called Bend communications manager Tawna Fenske. “Sounds sort of familiar?” she said. “Sorry. We work with so many influencers.”

Influencers often talk about their “communities.” Rarely, however, are these communities tested in an intimate, let’s-share-a-tent kind of way.

In an alternate universe, a travel influencer is—maybe—someone I would’ve been. My post-college career dreams also included getting paid to travel. Except my path followed a standard late-20th-century, Gen X trajectory that began with a cover letter printed on heavy cream-colored stock, mailed with two stamps to a Bay Area–based “active travel” company called Backroads. It sat in a slush pile with pleas from other white liberal-arts majors waxing unpoetically about why travel matters, until one day I was serving breakfast at a San Francisco café and I got a message on my landline offering me an office job as a marketing assistant. I’d track magazine ads, edit the website, and write weekly headlines for the company’s fax cover sheet (“Go Galápagos: Dolphins, Iguanas, Blue-Footed Boobies, Oh My!”). The salary, which hovered around the poverty line, included the perk of this 23-year-old’s lifetime: a free weeklong hiking, biking, or multisport vacation, in addition to the standard two weeks. I was sold.

My first free Backroads trip, to Yellowstone, was led—like all Backroads trips—by two affable, superheroic humans who had undergone a 48-hour audition that tested wilderness skills and charisma, public speaking and patience with pretend guests. Backroads’ guides were living, breathing, bicycling representations of the company’s brand. They carried bear spray, identified wildflowers, entertained, cooked, and cleaned—then woke before dawn and did it all again.

Post-pandemic, many of these old-school outfitters have seen soaring demand, largely thanks to their older, affluent demographic. The age of most Backroads guests is between 40 and 75. Whereas Trova travelers trend younger—mid-thirties, on average. Which makes me wonder: Will traditional outfitters like Backroads eventually fall out of fashion and ultimately go the way of the fax machine? Not one woman on Haleigh’s trip considered backpacking with a company. “I’d trust a person more,” Liz told me. It never dawned on them that they could’ve booked essentially the same trip with Wildland—without Haleigh—for $600 less. They wouldn’t have wanted to anyway.

Maybe it was the relentless trek or the altitude or the blisters, but as we sat around the campfire, sharing our highs and lows about the day, more than one woman was moved to tears. By doing something hard, they said. By doing something they never thought they could. By a passage Haleigh read aloud from one of her favorite books, Out Here, by Carolyn Highland. By just being in the wilderness, with a group of women. With Haleigh. Because of Haleigh.

Haleigh’s high? “Even though we were all going at different paces, I’m grateful I got to hike with each and every one of you today,” she said. Her followers were grateful, too. “Thank you, Haleigh,” someone said. “That did not go unnoticed.” Haleigh couldn’t believe her luck, either. Her community. “This trip has already exceeded my expectations,” she said. Beneath her perfect bangs, she was teary, too.

As the week went on, we did what backpackers do. Fell asleep under the stars and woke with the sun. Trudged over snowfields and sifted through our snack bags. Dunked in bone-cold creeks and click-clacked our poles along rocky trails. Gawked at waterfalls gushing out of granite nooks. We learned that Liz’s boyfriend had died tragically the previous summer and that Hayden’s father died a week before the trip started and that Dena was raised by a deeply narcissistic mom. We shared tales of bad breakups and good sex, career hopes and parenting fears. We belly-laughed and were bitten by mosquitoes and somehow never saw a bear.

The merry group in front of Half Dome (Photo: Jordan of The Homebody Tourist)

Haleigh enjoying the fading light atop Half Dome (Photo: Haleigh Hendrickson)

Sure, some did what influencers, or at least Instagrammers, do. Yoga handstands at dusk. Synchronized jumping. “Will you take a photo of me?” Amanda asked Haleigh one evening, clambering onto a boulder and posing with a perfectly straight back, head gazing right, long brown hair cascading beneath her knit Carhartt hat.

Throughout the week, Haleigh pulled each hiker aside, aimed her camera at their face, and posed the same question: “What’s your biggest takeaway from this trip?’ ” “What’s this for?” everyone asked. “You’ll see,” she teased.

Haleigh may have brought everyone together, but then everyone bonded on their own. “I don’t think they need me anymore!” she laughed. But the thing is: they did. “None of us would be here without you,” said Dena on our penultimate night. “You were the catalyst.”

“More women outdoors” is a tagline on Haleigh’s Instagram bio. It’s a worthy if increasingly unoriginal sentiment in the women’s travel-influencer world. Still, inspiring others is what gives an otherwise hedonistic, pleasure-seeking existence a higher purpose. (While, yes, also funding it.) “I don’t want people just looking at my life and being like, ‘Wow, I wish I could go on these adventures!’ ” she told me. “I want people—women—to have the opportunity to go on these adventures. I want them to be like: I can do this!”

On our last day, during a tedious descent back to the valley, Haleigh was stopped by a stranger, a Frenchwoman who took off her glasses and exclaimed, “You’re @wherewewentnext!” Switching excitedly between English and French, she was as starstruck as if she’d spotted an actual celebrity. “I can’t believe I am talking to you in person! I can’t believe you’re here!” She couldn’t believe she could’ve come here, to Yosemite, with Haleigh.

Soon we all made it down, back to the parking lot—where cheese and crackers, grapes and olives, dolmas and LaCroix awaited, arranged over a checkered tablecloth. It was a picture-perfect spread. Well, if you cropped out the yellow caution tape strung behind it, and the dude driving a giant digger near us, and the row of bear bins plastered with posters warning of hantavirus. Which everyone did.

I’d signed up for a week in the wild with an influencer and her fangirls, bracing for some sort of mashup of the Fyre Festival, Lord of the Flies, and The Bachelorette.

Why do you think people follow you? I asked Haleigh on our winding drive out of Yosemite, back to Indian Flat.

“I don’t know why, I really don’t,” she said. Maybe it’s because she was just a person who had barely 1,000 followers, she said, and then one day woke up with a gazillion more. “I guess people relate to my story?”

“But your story isn’t that special!” I said. No offense. “You’re not Taylor Swift!”

She agreed. “I’m just normal,” she said.

Then again, Swift, with almost 300 million followers on Instagram alone, may be the world’s preeminent influencer because she built her reputation on being normal, too. I guess people relate to Haleigh because she really is just a regular person. A woman who hated her job, quit, went camping—and got lucky with a lot of likes.

By the end of the trip, I felt lucky, too. I’d signed up for a week in the wild with an influencer and her fangirls, bracing for some sort of mashup of the Fyre Festival, Lord of the Flies, and The Bachelorette. Instead, I had fun. I even left Yosemite with new friends (or at least a new group thread, titled “Yosemite”), and something perhaps more lasting: a new faith in online humanity.

People aren’t always what they seem, on social media especially. Haleigh, though, as everyone reiterated throughout the week, is real. “She’s exactly the same person online as she is in person,” said Jeanne.

I don’t disagree. I’d been expecting to witness some sort of dissonance between Haleigh on Instagram and Haleigh on-trail. An eye roll or a terse retort, constant primping, incessant posting. But no. Haleigh was just super nice. Still naturally pretty in the dirt on day six. And, in fact, iPhone-free. She was the only one who didn’t pull hers out once all week. “I’m so sick of my phone!” she said. She lugs around an actual camera instead.

I’d assumed that I’d come home telling everyone that traveling with an influencer and tagging along on her dream life was a total nightmare. That, yup, it’s true: Instagram makes everything look better than it is. Instead I came home, cozied up with my phone, and concluded the opposite.

There were Liz and Jordan doing their complicated choreographed handshake all over Yosemite. There were the two Kelseys in Carhartt hats, kicking up their heels at the count of three. And the flickering fire pit, the thundering falls, and the alpenglow illuminating Half Dome. And multiple mugs of coffee clasped by multiple hands. And there was everyone, backed by towering granite: beaming into Haleigh’s camera, sharing their takeaways. “Never be afraid to push your limits.” “I can do harder things than I ever thought I could.” “If you let people in, they will make room for you.” There was Dena doing a happy dance and Jordan hoisting her Hest pillow into the sky for $300.

I watched the handshake half a dozen times and played Haleigh’s reel on repeat and couldn’t help but smile, too. If I hadn’t dusted off my backpack and gone on this trip, I probably would’ve viewed this random travel influencer’s feed like I do all travel influencers’ feeds: with a mix of envy and irritation. Then I’d scoff at the absurdity of it all and scroll to the next one.

Instead, I felt the spray of waterfalls and chatted on a log in the sun and swung in a hammock strung between pines (it was brought for everyone, after all). And months later, as I lay on my couch thumbing through every perfect post, I realized my takeaway: Yosemite with Haleigh was actually more fun IRL than on IG.

From July/August 2024

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Lead Photo: Courtesy Trovatrip

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