Airbnb has taken on hotels, now it’s gunning for the whole travel industry with Trips


At the core of the new Airbnb is a curated list of more than 500 trips covering 12 cities worldwide

elderly man in his underpants stands waist-deep in azure water playing The Blue Danube on a violin. Behind him, San Francisco Bay is littered with boats bobbing listlessly under the fading vapour trails of the Blue Angels demonstration squadron. On the surrounding scrubland, families out to watch the airshow pack up their deckchairs and tumble into the Sunday afternoon traffic. It is, perhaps, what Airbnb co-founder and CEO Brian Chesky would describe as spontaneity.

“The problem with travel, I think, is mass tourism,” says Chesky. And, in true Silicon Valley style, he’s out to solve it. The launch of Trips, the biggest change to Airbnb since its founding in 2008, is Chesky’s attempt to take a much bigger slice of a multi-billion dollar industry. “We want to reinvent the trip,” he says, without a hint of hubris. And by reinventing the trip, Chesky is also redefining Airbnb’s future.

Co-founder and CEO Brian Chesky describes Airbnb Trips, the startup's biggest launch to date, as “mass-niche” tourism

Co-founder and CEO Brian Chesky describes Airbnb Trips, the startup’s biggest launch to date, as “mass-niche” tourism. Credit: Airbnb

At the core of the new Airbnb is a curated list of more than 500 trips covering 12 cities worldwide. Activities range from truffle hunting in Florence to surfing in Los Angeles and photography in Nairobi. “Travel is one of the most aspirational things in the world,” says Chesky. “And yet when you look at what the internet has done: it’s made it cheap, it’s also made it a commodity.” It all started with the grand tours of Europe, he explains, when upper-classes exposed themselves to the finest culture the continent had to offer. Fast-forward 200-odd years and something’s been lost in translation. “It got shorter and shorter and shorter and mass produced, and now the notion of participating and learning painting is limited to going to the Louvre and looking at like 5,000 paintings,” he says.

Chesky describes his plan as “mass-niche” tourism. Everything on the Trips part of Airbnb will be selected by a human, not an algorithm. Airbnb has even hired professional videographers to shoot promotional trailers for every experience. Sweeping shots of forest walks are matched with epic music and toned, athletic models. There are two major differences between the old Airbnb and the new Airbnb: when it comes to renting out a home or room, it’s an open marketplace; everything else being added to Airbnb with the launch of Trips is curated. And all the experiences, from LA taco tours to boho beach parties, will be Instant Book. “A trip can actually be designed,” says Chesky. “There’s a sequence to things.”

But there’s a contradiction in Chesky’s vision, a sort of managed spontaneity. A holiday where you experience new and unusual things, go off the beaten track, but only do so on a pre-booked experience you’ve found through the world’s third most valuable private company.

Baker Beach, San Francisco

Baker Beach, San Francisco. Credit: James Temperton/WIRED

One of experiences available at launch is “Zen Explorers”, a $150, three-day trip hosted by “mindful mavens” Nicki and Pam, with the help of some friends. As Pam explains, it’s exciting to be part of the launch, but getting involved with Airbnb does have its downsides: she can no longer cook the food she serves – everything has to be from state-approved restaurants; everyone on the trip has to sign a waiver against “paralysis, death or damage”; and at $150 per person, of which Airbnb takes a 15 per cent cut, profits for hosts are low. It’s easy to understand why: the trip includes three meals, a guided, meditative hike through Muir Woods and an excursion to the Golden Gate Bridge in an outrigger canoe. The latter is the highlight. The day starts with a crash-course in paddling on the deck of Pam’s houseboat on the outskirts of Sausalito, followed by a paddle to Horseshoe Bay and a burger at the Presido Yacht Club. Then there’s the unexpected appearance of the near-nude violinist.

Chesky describes the launch of Trips as a “step-change” for tourism that will be powered by “people and communities”. And, to an extent, that’s true. Had I come to San Francisco, visited Fisherman’s Wharf and eaten clam chowder at Bubba Gump Shrimp Co. I would have had a lousy time and some lousy chowder. What Airbnb is trying to do is make tourism more offbeat, but do so at scale. “You often don’t go off the beaten path with mass tourism,” says Chesky. “Here, you’re going to be able to step out, there’s spontaneity.”

Muir Woods, Marin County, California

Muir Woods, Marin County, California. Credit: James Temperton/WIRED

But, by attempting to commodify authentic, unique experiences, Airbnb is creating a contradiction. The marketing gloss applied to each of the 500-odd experiences available at the launch of Trips gives them an almost blockbuster feel. Chesky says Airbnb will “merchandise” Trips. “It’s like a Hollywood production in here right now, it’s incredibly fun,” says Alex Schleifer, Airbnb’s vice president of design. “We’re creating hours of films. We’re creating custom illustration and we’re doing typography and cartography,” he explains. “Our whole mission is to create this human-powered, emotional, transformative way to travel. And I think that trailers are going to be what represents that.”

For the Zen Explorers weekend, Airbnb hired a group of models who posed for promotional photos and videos. Once the Golden Gate Bridge paddling shoot was finished, Pam jokes, the models refused to row the boat back to land. “We will one day forget and take for granted that we can completely immerse, that you can virtually experience something before you go there,” says Chesky, referring to the hundreds of hours Airbnb has poured into creating promotional materials for Trips. “Is that a marketing gloss? I don’t think it is. But we are definitely trying to set a standard of quality that doesn’t exist today.”

Behind the heavily-curated, human-reliant frontend, Airbnb’s backend is also getting an upgrade. “Homes don’t actually give you all that much information to personalise on,” says Joe Zadeh, Airbnb’s vice president of product and longest-serving employee. But that’s starting to change. Airbnb is collecting more and more data on its users and listings. User reviews are helping to build accurate profiles of rooms and properties, while people’s preferences and habits are informing what they see on Airbnb. Once people start booking adventure weekends, restaurants and gigs through Airbnb, says Zadeh, those profiles will get even more detailed. “Today, if two people search for San Francisco, depending on your history on Airbnb, you’re going to see radically different things based on what we know about you. And our goal is not to make that obvious. Our goal is to make it really fast for you to get the right place.” And that’s the hard part. On August 13, 2016, 1.8 million people slept in an Airbnb bed. If Trips is even a fraction as big, it will need to lean heavily on big data.

Airbnb co-founder and CEO Brian Chesky says mass tourism has over-commodified travel

Airbnb co-founder and CEO Brian Chesky says mass tourism has over-commodified travel credit: Kimberly White/Getty Images for Fortune

For that challenge, Zadeh gets his team to work in reverse. Start with something that doesn’t scale and work out how to make it scale. “Instead of starting with scale and adding things on top, why don’t we start with what a great trip looks like and scale that?” he says. “Don’t try to just do something with the data, actually start backwards: what does it mean to feel like you have inside knowledge of a city you’ve never been to before? I think we tried to apply that as much as possible.” It’s a mantra repeated by Schleifer. “We won’t recommend you the same thing everybody else recommends. The dream, whether it’s attainable or not, is that everybody’s itinerary, everybody’s recommendations, would be entirely different.”

Airbnb’s attempt to scale unique, authentic experiences throws up a familiar quandary with its homes business. Neighbours complain of homes being turned into hotels, while Airbnb-heavy neighbourhoods risk losing some of the local, authentic charm that made them so popular in the first place. “We approve most of the experiences that happen,” says Chesky in defence of Airbnb’s launch of Trips. “And we don’t want to approve so many experiences in such a small area that this would happen. Trying to better design our platform to redistribute is key.”

With Trips, Chesky believes Airbnb can move tourists away from tourist traps. It’s this belief that travel is broken that has seen the company’s value swell to more than $30 billion off the back of its homes business. But Trips is something quite different. It is curated, it is merchandised and it is meticulously designed. Airbnb’s contradictory gamble is that it can scale spontaneity. Standing watching the near-nude violinist it occurs to me that I’ve seen a different side of San Francisco. But how different will it feel once thousands of other tourists have opened the Airbnb app in search of something unexpected?

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