Booking keeps coming back to the same idea: the connected trip.

Can AI get them there?

The hardest thing about the connected trip in ecommerce is that people traditionally just don’t book everything in one go. But what happens when your AI agent is doing the booking?

We see this playing out in the Booking Q2 numbers and the role of AI in its connected trip strategy. We’ve also been hearing about it for a decade.

The headline market stuff is fine - revenue expectations, growth, volatility, all the public-company theatre. But perhaps the more interesting bit for travel is that Booking is using AI to pull more of the trip into one operating system.
 
“AI in travel” can sound like a chatbot sitting on top of the old funnel. Booking’s version is perhaps more useful than that. It is about accommodation, flights, ground transport, attractions, customer service, payments, loyalty and post-booking help starting to behave less like separate tabs and more like one trip record.

Airbnb deciding to rent out Viator’s tour inventory show us that maybe everyone is suddenly rushing for the same door. The response to an AI query can’t be: “I don’t know, we don’t sell that here.”
 
Are we there yet? NO. But this is the clear direction of travel. The companies with enough demand, supply, data and servicing infrastructure are trying to turn AI into the layer that joins the trip together. Not just answers questions. Joins things together.

What we are building at reely.travel I think fits neatly with this picture. We have what the traveller has self-curated through their saved Instagram reels and TikTok's. This is destinations, hotel choices, experiences desired, restaurants salivated over. The things the travelling party have put firmly on their intention list. When they add dates - we suddenly can present the whole picture - not just to them but to anyone who has the ability to quote the whole trip. That could be Booking.com or Expedia Group or a client of Amadeus or an advisor at Fora Travel or Flight Centre Travel Group.

It can be anyone that can provide a timely quote back via their agentic capabilities (and by timely - I mean near instantly). Not piecemeal. Not over time. The whole trip. Now.
 
This content is provided by the newsletter sponsor reely.travel - leading the travel industry to A2A negotiations in travel. Save reels, then save money. Yes Reely.

More than half of active US travellers are now using AI for travel

56% is latest figure according to Phocuswright. But what does “using AI” actually mean?

Does it mean someone opens ChatGPT as the first port of call and asks where to go? Does it mean they type a normal Google search and read the AI Overview before clicking anything? Does it mean they use an OTA’s embedded AI planner? Does it mean they ask an LLM to compare hotel prices, rewrite an itinerary, sanity-check a connection time, find activities near the hotel, translate reviews, or manage something while in destination?

Those are not the same behaviour. Not commercially anyway. And it is commercially that businesses will be making decisions.

So whilst Phocuswright’s own summary says 56% of travellers used AI for planning, booking or in-destination assistance for at least one trip in the past 12 months, what we really need to know is how much is top of funnel discovery. How much is mid-funnel comparison. Is there any bottom-funnel reassurance or conversion support. One is post-booking service. If we just bundle all of that into “travellers are using AI”, we miss the bit travel businesses actually need to understand.

The problem is that a ChatGPT-first traveller, an AI Overview reader, and someone using AI to check whether a price is fair may all show up in the same adoption stat. That makes the number impressive, but also a bit slippery if making big investment decisions.

That is the distribution question for travel. If AI is influencing the shortlist before the traveller reaches you, you need to know whether you are being discovered, compared, validated or quietly excluded. And if your hotel, tour, destination, advisor, OTA or supplier is not understandable to AI systems, you may not even make the conversation.

Businesses should ask where in the journey AI is being used, what sources are shaping the answer, whether their own content answers real traveller questions, and whether third-party proof exists outside the brand website.

Let's not also forget that the most recent Skift research suggested 83% of people use social media for their destination inspiration. 83%! And yet very few are making investments in social to show up when those searches are made. So let's not think a big reported number will make companies suddenly jump - even when they probably should be.

Mike from PhocusWright tells me the answers to this are in the research itself. Maybe therefore worth spending a little on research before spending a lot on execution in case you are building in the wrong direction!

AI is not the only answer of where to find your customers - but it is one of the answers

The old simple front organic door was SEO. “Booking Holdings CEO Glenn Fogel said Tuesday that the company saw pressure on organic search results from Google's AI Overviews in the second quarter, although it is a small part of overall business.” as reported by Skift.

The old travel agent gave you the advice and took the booking. Online travel split those jobs apart. (Fora might argue the old travel agent is not that old).

Now people get advice from Instagram searches, TikTok, forums, Reddit, friends, creators, AI, whatever else is open in the 43 tabs of doom - and then go somewhere else to book.

We have spent 25 years making booking faster, cheaper, more measurable and more optimised. This is great. Except the messy human bit before the booking - inspiration, trust, comparison, vibe checking, reassurance - still leaks all over the internet. Those pesky humans are hard to tie down.

AI does not magically fix that. In some ways it makes the split more obvious. If the traveller asks ChatGPT, Perplexity, TikTok, Reddit or some future agent what to do, where to stay or which tour to book, the booking brand may only see the customer after the decision has already been shaped somewhere else.

Agoda’s Tim Hughes calls this the Reddit dilemma

This is not just an OTA problem BTW. Hotels, tour operators, DMOs and travel brands all have the same issue. If your useful advice, proof, content and third-party validation are not showing up where people are actually deciding, your booking engine can be beautifully optimised and still arrive too late.

The front door is moving again.

For mine, this is where AI search and social search start to look like the same commercial problem. The traveller is building confidence before they click book. They always have. That 'old' travel agent came with that built in.

Your job is not only to transact. It is to be present, useful and believable inside that messy consideration set.

Maybe a good time to check where your customers are getting advice before they get to you. Because if the answer is “not from us”, someone else might be doing the most valuable bit of the sale - deciding who to buy with.

On the social side, here is a simple check you can do right now in under 10 seconds: Search your core keywords in the Instagram search box - do you see your brand in the answers returned? Do you see your competitors' brand? Start asking why that is.

(Note: we fix this problem for our customers at CollabsMap. Take a look at how we help Max Tours show up twice in the first 5 results for their core key words).

Now is a good time to check if the backdoor is locked

You know the old trick of slipping the maitre’d a Benjamin for them to fit you in at a fully booked restaurant? Now you might only need Open Claw and Claude.

I wonder how many reservations systems might unknowingly be able to be hacked to fit you in - by kicking someone else out.

If I owned one, I’d be trying to hack myself first before finding out someone else had exposed that vulnerability.

I generally don’t like AI video for travel but……

This is pretty freaking cool. AR/VR has been pretty much a bust in travel and will probably remain so - but still…

If you think someone (or everyone) you know or work with could grow from being more informed on the topic of ai + travel (or could use the training above) then please forward this email to them and they can click the button below:

To get a glimpse into our travel future, keep an eye on ecommerce

Shopify put out some info this week that I think people should be paying attention to.

“More and more shoppers are describing what they need to an AI assistant and letting it do the legwork instead of scrolling a results page and clicking into sites themselves. At the same time, organic search is still one of the largest discovery channels in commerce.”

Shopify is probably the developer world’s biggest playground. You have one set of rails, one unified data structure and then pretty much any product someone could buy at the end of it. Empires have been built servicing Shopify merchants.

This from their blog this week: “what makes someone choose AI search versus organic search?” Shopify’s Q2 commerce data offers one possible read. It comes down to the job the shopper is trying to do:

• AI and organic search are both growing. AI-referred sessions to Shopify storefronts grew 197% year-over-year, while organic search grew 12% on top of a much larger base.

• AI is growing everywhere, but impact concentrates on research-intensive journeys. In spec-led categories, AI-referred shoppers convert at about double the rate of organic search.

• The same optimization work benefits both search surfaces. When AI drew on structured Shopify Catalog product data, the shoppers it referred converted 2x better than those from scraped or third-party feeds.

Would we say travel is a research-intensive journey…………. hmm.

Here is what Shopify President Henry Finkelstein had to say about the information in the post:

“This is what the billion dollar brands of the next decade are focused on now.

AI search.

AI is the new discovery channel. Both traffic and orders to Shopify stores from AI channels have tripled since last year. It’s small today, but it’s growing fast.

And here’s the best part. AI search is not fighting traditional organic search.

It’s complementing it.

In fact, shoppers are using it to do very different jobs.

And, I cannot stress this enough. If you are running a business in 2026. You. Need. To. Know. This.

There’s a lot in the report, but my top takeaway was this:

AI search is conversational.
Shoppers don’t talk to their agent in keywords.
So you shouldn’t either.”

Slack Group!

Podcasts and Sponsors

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