When Your Favorite Influencer Becomes Your Vacation Buddy

In 2022, Ali Jackson went on a 35th birthday trip to Colombia with seven of her closest friends. They sipped drinks in the pool, shopped the streets of Cartagena, took a boat ride through the Caribbean Sea, and — as one does — showed it off on social media. Jackson normally posts about dating under the moniker Finding Mr. Height, helping her Instagram followers (48,000 and counting) and Patreon subscribers (she has a podcast of the same name) with everything from wedding etiquette to STI dilemmas. But as her followers lived vicariously through her vacation pics, they started thinking about finding a very different kind of relationship.

“I was getting so many messages from my followers saying things like, ‘I wish my friends wanted to do this,’” Jackson says.

Jackson had seen ads for TrovaTrip, a marketplace for creators looking to host vacations for their communities, on her own Instagram feed, and figured this was the time to try. She decided on Greece, and on June 3, 2023, Jackson and podcast co-host Erica Spera departed for Santorini along with 19 followers whom they had never met. “These people know a lot about me,” Jackson remembers thinking. “I know nothing about them.”

Jackson is one of many creators who are now taking the online communities they built during COVID into real life — and tapping into a moment when followers are especially eager for connection. In an op-ed for the New York Times in April of this year, U.S. Surgeon General Vivek H. Murthy declared an “epidemic of loneliness,” one that had been brewing long before COVID. Amid that, companies like Flash Pack have stepped up to facilitate trips for forming adult friendships among millennial clientele. TrovaTrip, founded in 2017, has seen 2000% growth since the pandemic, according to a spokesperson, and expects to run 500 trips in 2023 alone. Other creators skip the middleman, like Maria Avgitidis. She’s the CEO of matchmaking service Agape Match with an audience on Instagram, fielding dating questions from her over 55,000 followers. She has been hosting different versions of retreats since 2012, all of which are run through her company. “As a matchmaker, my job is not just to help people find love,” she says. “I think it’s just to help people find their people, and that might be also in friendship.”

A few years ago, announcing to your friends that you were paying to go on vacation with an influencer might have attracted some raised eyebrows — and, indeed, perhaps in the shadow of recent influencer controversies like Tanya Zuckerbrot’s F-Factor diet and Caroline Calloway’s ill-fated “Creativity Workshops,” there are still concerns about scams and too-good-to-be-true advertising. But remote work and other pandemic workarounds mean digital relationships, even one-sided ones, have taken on a new significance, and content creation as a career path has only gotten more visible and legitimized. Internet celebrities now walk the Met Gala carpet alongside actors and singers. Even your mom probably follows a few influencers by now.

Compared to those traditional entertainers, influencers often have a more intimate and active relationship with their followers, in part because their income depends on it: Brands throw money at creators in hopes they can turn their followers’ enthusiasm into clicks or attention. But companies like TrovaTrip had a hunch followers would do more than just use a promo code for their favorite creator — they’d travel across the world.

“One of the dogs took a massive toilet break on the grass and I was on my hands and knees picking up the sh*t.”

In the case of Christy Anne Jones, an Australian writer and YouTuber who makes videos about reading and her novel-writing process, TrovaTrip reached out to her. It was still the early days of the pandemic, and the idea of playing host had never occurred to her. But Jones realized this may very well be the only way she and her followers, most of whom live in the U.S. and the U.K., could ever meet in real life.

The first step for any TrovaTrip is to have the creator survey their community to ensure there’s enough interest. Once they get 50 responses from adults with a budget of at least $2,000, they can choose from a number of locations and itineraries provided by independent tour companies, known as “operators,” that have been through a “rigorous” vetting process, TrovaTrip co-founder Lauren Schneider says.

Jones, with survey input from her followers, landed on Japan, a place she had previously lived and written about in her book, A Year in Tōkyō: An Illustrated Guide and Memoir.

For the price of $3,295 each, 20 followers joined Jones in May on a seven-day trip across Tokyo, Kyoto, and Osaka. This fee included transportation to and from the airports, overnight accommodations, around half of the meals, and activities like walking tours and sushi-making classes. The creator is in charge of setting the trip price, Schneider explains, and they earn 20% of the revenue on average, while TrovaTrip earns 15% to 20% and operators earn the remaining.

That means creators can often get a five-figure payout, potentially earning thousands of dollars per day, just to play host — which, when you’re on a Mediterranean island, doesn’t sound like the worst day at the office.

But it’s also not purely a vacation. Creators participate in the entirety of the trip: “I was a little bit nervous that it would be like a celebrity appearance,” says Lissa Skogstad, who attended Jackson’s trip to Greece. “And it was not like that at all. They hung out with us the whole time.”

For hosts organizing trips outside of a company like TrovaTrip, it can be even more work. Lindsey Holland, a London-based lifestyle creator who founded the surfing and wellness retreat company Marnie Rays, says she was responsible for finding, vetting, and organizing every detail down to the tableware at their retreats this summer in Aljezur, Portugal, where guests enjoyed a five-night villa stay, guest chefs, surfing lessons, and yoga classes for $2,831 per person. “There isn’t anything I didn’t do,” she says. “One morning we were setting up for breakfast and one of the [stray] dogs took a massive toilet break on the grass and I was on my hands and knees picking up the sh*t.”

Both Marnie Rays and TrovaTrip, however, have a similar process when it comes to security. All attendees must be approved by the hosts before they can start packing their suitcases, and hosts know to take the process seriously.

“When you create content online, sometimes you’ll have people who aren’t particularly kind to you or they can be a little bit inappropriate sometimes,” Jones says. “And so everyone who went on the trip, I Googled them and I double-checked.”

Jackson, who’s already sold out a similar trip to Costa Rica for April of next year, similarly vetted her attendees by searching their Instagram usernames, which they provided, in her messages to make sure they hadn’t had any uncomfortable interactions. She also kept the trip as women-only. Holland took the sleuthing a step further, not just for security, but also for a vibe check — looking to see if guests had a recent birthday, or a pet they’d be missing — so she could reference it in the personalized notes she gave them upon arrival.

None of the hosts I spoke to needed to turn away a guest for security reasons. Instead, their main concern became whether everyone would mesh — one that would turn out to be unfounded.

“I had brought little icebreaker cards and I put them on all the tables at the welcome dinner,” Jackson says. “No one touched them, in a good way.”

“Anytime anyone wanted a picture of themselves, there were at least six girls telling them how great they looked and telling them to do different poses.”

Following the same influencer, it turns out, can be a far more accurate compatibility test than whether you watch the same TV shows or listen to the same music. It can be a serious time investment — you’re consuming a steady stream of new content, often over years — and reflects a shared sense of values and lifestyle goals outside of screen time.

“It’s like you’re meeting a friend of a friend, right?” Jones says. “You’ve got this key pillar between you, so you're probably gonna gel in some kind of way.”

Plus, creators like Jones and Jackson have cultivated communities around specific interests and activities. Because Jones makes content about books and writing, her Japan itinerary included multiple bookstore stops. “The bus ride from Osaka to Kyoto, it was just 20 people all reading physical books,” she remembers.

For Jackson, the dating focus of her content offered countless entry points for bonding — there’s no icebreaker quite like commiserating over bad dates or polling each other for advice about a situationship.

“Right away, everyone hopped in to take photos of each other for dating profiles,” Skogstad says. “Anytime anyone wanted a picture of themselves, there were at least six girls telling them how great they looked and telling them to do different poses. It was just a really fun atmosphere and that happened really naturally.”

The influencers themselves are not always the biggest draw. For many guests, the motivation to finally hit “confirm” was the lack of similar travel opportunities in their own lives. Maybe they either didn’t have a group to go with and were intimidated by traveling alone: Holland was inspired to start Marnie Rays after attempts at solo travel made her uncomfortable. “I was like, ‘I can't do this,’” she remembers. “‘I don’t know if I can be alone. I feel so weird.’”

Or maybe they just needed that extra push — in the form of a content creator they trusted — to do something on their bucket lists. “I'd never been out of the country before,” says Carly D'Alessio, who also attended Jackson’s Greece trip. “I had this goal that when I was 25 that I would do that.” (She turned 25 this year.)

Still, the relationship between host and guests was one of the biggest question marks hanging over the trip. Jackson, for instance, was worried that her candor in sharing her life online would mean travelers could feel entitled to personal information she wasn’t comfortable divulging. But she says that never was a problem — probably because the attendees were just as nervous about that relationship.

“That’s something that I wanted to be mindful of on the trip,” Skogstad says of Jackson’s Greece getaway. “Letting her maintain the space that she wants to with any of us.”

“I think in order to not make it weird, we just didn't really acknowledge it,” Jones says of her own role as host. Rather than think of it as a creator and her followers, the group made the unspoken decision to embark on the trip as equals. It wasn’t until the end that some of the travelers asked Jones to sign copies of her book.

Since any kind of relationship with a creator takes place online, followers say the transition to in-person interactions could feel surreal. Skogstad remembers one time when she, Jackson, and the rest of the attendees were sharing a meal.

“‘This is so funny,’” she said to Jackson. “‘This is like when you eat on [Instagram] Live and I'm eating at home while you're eating on Live.’”

“You just see them more as a human.”

“I still tear up thinking about the posts that people were doing after the trip,” Jackson says. “Every single post from a traveler was like, ‘I can't believe I showed up to Greece eight days ago and met 20 strangers that are now my closest friends.’”

“We've heard stories of travelers going on to become roommates and get married,” says Schneider, the TrovaTrip founder. “One of our early hosts, she met her surrogate on TrovaTrip and now has a baby because of it.”

Attendees say they’re still in touch via group chats, and many continue to meet up long after touching back down on home soil. Holland says one of this summer’s Marnie Rays guests is a musician, and fellow travelers from her retreat have come to her gigs.

“Even I have made two really good mates, they live down the road,” she says. “And we’ve been really close since we've been back. I’m like, ‘Oh, I’ve got friends out of it too.’”

And while it might be weird for attendees to go from follower to IRL friend to back again, many of them say they’ve stayed in touch with the creators and have plans to meet up with them as part of another get-together, or at least would feel comfortable reaching out to grab dinner the next time they’re in the same cities. “You kind of just see them more as a human, I guess,” D'Alessio says.

But even if they don’t end up crossing paths again, the experience of being their follower has been forever changed. “I look at her now like she's like somebody that I just know,” Kathleen Collins, a Marnie Rays attendee, says of following Holland. “So there's less of this like, ‘Oh my God, it’s so cool.’ I'm like, ‘Ah — good for her!’”