Airbnb's new 'Icons', AI Travel Planning, and the future of Experiences

The Airbnb summer release is here, with the launch of 'Icons' front and center. Brian Chesky owes Steve Jobs a royalty check for this presentation. Amazing storytelling in the “but there’s just one more thing” Apple tradition. I was waiting for his black shirt to sprout a turtleneck halfway through.

In short, for 2024, about 4,000 people will get to book extremely unique Airbnb lodgings like the Disney-Pixar 'Up' house, or gain special access to unique experiences like viewing the Paris Olympics opening ceremony from the Orsay museum (after spending the night there). They're all no or low cost, meaning this is just "something cool" and not a business strategy. It's reminiscent of the reboot of GetYourGuide Originals—very special, very unique, very memorable. But self-admittedly not meaningfully scalable.

So, zooming out a bit—and given I view all of this from the tours & activities space I work in—I thought I'd share some thoughts at what the launch of Icons and continued hints at AI integration could mean for the future direction of Airbnb Experiences, and travel planning?

1. When it comes to Experiences, Airbnb continues to be the ultimate tease. Once again… next year Airbnb promises “something really big coming out” (see Dennis Schaal's Skift article) re: Experiences. At only 4,000 “invitations” to Icons, this launch is just a glorified press release and another tease of a future for non-lodging Airbnb products. We in the tours & activities space remain in an eternal holding pattern of hoping something’s truly next and great with Airbnb Experiences. I'd gladly offer to make the coffee for the team if it means accelerating this multi-year holding pattern we're all in. Experiences sits as a tour marketplace unlike any other OTA, I want to see it flourish.
2. From a psychological standpoint, with Icons, Airbnb’s hit on something essential: people travel for magical moments, for stories they’ll go home and share. This is much more than thinking of Icons as just "set-jetting" or fanboy travel. From a travel planning POV, Icons can ignite a “travel spark” — the 'marquee experience' that captures your imagination and gets you motivated to go somewhere. Certainly that travel spark is often (these days) connected to a movie, an event, or a kind of lodging (I want to stay in the Barbie mansion or a milk bottle in the middle of the desert). But I’m currently in Mexico City, and my spark was wanting to see Diego Rivera’s murals. An Airbnb Icon is what I more prosaically call a “wow moment” — the one moment of a trip that will be remembered after all is over and largely forgotten. Our industry is really bad at understanding this fundamental fact about human memory and psychology (read the late Daniel Kahneman on the peak-end rule) and how the customer journey can be better designed around it. I could see a more scaled (and less elaborate) version of Icons in which Airbnb creates these elevated Experiences as a way to address travel inspiration in thousands of cities for thousands of niche communities—and developing these would be another way (along with unique lodging) to drive demand to lesser-visited destinations.
3. Airbnb has the ability to offer an interesting approach to travel planning where all the AI planning startups currently fail. They already have the data for useful customer personas. So, on the bedrock of the accommodation booking, with an inventory of unique experiences, Airbnb could create a great, seamless multi-day itinerary (they just need a ticketing partner to fill in the attractions component) for those personas. And they could harness the knowledge of their local hosts in terms of food recommendations, a huge pain point for current AI travel planners (and travel search in general). Customers are paralyzed by too much choice (googling around for everything, hitting bad or inauthentic advice), but they also don’t want no choice (e.g. current travel planners spitting out a bloated, soulless itinerary with generic activities and recommendations). Harness the perspective of local hosts to limit food and activity choices, peppered in with their own inventory of curated Experiences. Airbnb is uniquely positioned to do all of this seamlessly, and with personalization and personality/soul.
4. To accomplish this they need more standardization of their Experiences inventory/hosts. I think they landed a little too hard in the direction of ‘unique’, leaving the customer to book beer tastings in tree houses, and ran into a scale problem. They don't need to go towards total commodification (like Headout, for example), but they could learn a lot from their near-competitor Withlocals , which offers a similar “hang with a local” vibe, but via standard categories — the “city introduction” tour (perfect for when you’ve arrived at your accommodation), a food experience (great for the next day), and a hidden gems experience (for later in the week), + other key location-specific tours (day trip to the pyramids in Mexico City). Add to that an Airbnb “icon” experience (the peak ‘wow’ of the trip), and you don’t need much more. Bring in museum/attraction bookings via API, and voila, you've done the heavy lifting. Leave the rest of the time to the travelers figuring it out, and spontaneity. Meet the traveler in the middle—don’t try to fill all their time, just the right parts at the right times, with a curated set of trustworthy choices (the main problem in planning with uncurated marketplaces). And if Airbnb knows when I’m arriving at my accommodation, and knows I like to book private tours, why not offer a private host to meet me at my lodging and begin the city experience from there on Day 1? Who else but Airbnb could offer such a seamlessly executed customer journey, from inspiration to booking to experiencing?
5. Most Experiences hosts need more & better training. I'm certainly biased since I run a tour guide training school, but most Airbnb experiences I take from local hosts I leave with the impression of having enjoyed it, but it would've been so much better if the host was better trained in customer service, experience design, and guest engagement. Many professional tour operators (with well-trained guides) don’t use Experiences because there’s no connectivity with restech (amongst other issues), meaning they've lost a huge set of inventory with quality guides. Airbnb made this choice deliberately. But they didn't follow up with a meaningful quality control program. Besides the professional guides on the platform (who sometimes suffer from overtraining and an inability to think outside of the standard information-giving paradigm), Airbnb is missing the mark, given their reputation as the product-obsessed company.
6. Icons shows the power of connecting with communities, and community-based marketing. Connecting with the infinite varieties of fan and interest-based groups is a really great way for Airbnb to think about Experience's scaling problem, and an important reminder for tour operators that building and speaking to loyal communities is the future of experiences marketing for many small businesses at a time when PPC/Meta/Search is increasingly expensive and broken.

I understand that business decisions butt up against this potential future vision of a more integrated role for Experiences, but other than that, I'm curious if I'm completely missing the mark here.