A couple of quite large online travel agencies have been harping on about the “Connected Trip” for a long time and talk about it like it's something they’re working on. It's a fantastic objective, and most people would agree it makes a lot of sense, and those two OTAs ought to own the vast majority of the space.
I imagine the “Connected Trip” as an app that helps you from the start of booking a trip, throughout the travel experience, until you get home again.
It knows your flight details, alerts you of changes, remembers your favorite type of hotel room, helps you check-in and recommends where to get the venti, half-sweet, non-fat, iced mocha with light whipped cream and chocolate shavings on top that you need daily.
After that, it ensures you don’t get lost, books you a Segway tour, and alerts you on the need to book early bird tickets for the Eiffel Tower, or the bridge climb, or whatever. For three fun-filled days, it helps you spend all the money you planned on spending, and keeps 25% commission as a convenience fee. At the end, it helps you book transport back to the airport. And again from the airport back to your home.
It’s a beautiful concept. Your on-the-ground, always-there assistant is where a brand can create real loyalty, with all those extra touchpoints, rather than a long string of flight delay notifications. It is, or should be, a worthy objective for all major travel brands.
In reality, it hasn’t advanced all that far. The closest the industry has come is the traditional (often European) tour operators, with in-destination reps, welcome briefings, bingo nights (really!) and liaison with the local police if you get a little too rowdy.
In the digital world, we imagined Expedia Local Expert might take this space after they expanded out from the hotel desks. But these were cut in 2009, and the last of them given up during COVID.
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So in real life, where are we? Those OTAs seem to have stalled after figuring out how to remember your room preference and loyalty ID. They may even know about your flight. Maybe they link the two – Super PNR! – and when your flight is delayed, they alert the hotel that you’ll be needing a late check-in. (It doesn’t matter that the hotel doesn’t care when you check in, and if you try to change the date because of a 12-hour flight delay, then, oops, that's not within the cancellation window so – good luck!
All of your preferences in a nice big database, and at some point they’ll add the feature to recommend the kind of coffee you ordered on a trip to Paris four years ago and cleverly calculate that you’re an enthusiast of tall, 19th century steel towers.
So it hasn’t happened so far, and it’s not going to happen. There are two problems. One new. One not.
Experiences & local contracts
The Connected Trip must include activities in-destination. Experiences. Restaurants. Things-to-do. The reason you traveled in the first place. The two large OTAs have moved away from this space. It was too complex. Not enough money. Easier to contract out. On a direct, single transaction basis, it makes sense – the hotel people never liked those pesky experiences; they pushed shopping cart abandonment rates up, and that’s definitely a no-no.
The challenge inherent in the “connected trip” is the challenge of being … connected. Talking to your customers. Without direct relationships, the communication lines in this space are far too broken to expect to be able to serve up relevant activities with any value over and above a fresh Google search, which is a task most customers have a fairly good grip on.
Data - Customer Preferences
I’m tired of the data argument. Data that promises personalized travel planning and specific recommendations based on a few years of random bookings of trips. It's a fantastic pitch. It looks great on a presentation on PowerPoint slides at a conference. In reality, it’s mostly a nice story.
We all have numerous travel personas. Business, leisure, with the family, away with the boys, weekend with the girls, getting away from busy life, looking for adventure — who knows? There aren’t that many patterns to generate good, targeted recommendations. Don’t we travel in the first place to do something different? Nobody ever solved this, and nobody will. Now, nobody needs to.
The upcoming solution
As of December, anybody with a cheap laptop in their parents basement can access more information than was previously stored by all travel companies combined.
OpenAI has already probably read every review on Tripadvisor. (Sorry Tripadvisor, but the content generated with the help of 1 million suppliers has now been turned to open-source information stored in the brain of a computer, and it will never forget one word. Ever.) It knows every product on Viator and GetYourGuide. It read all of Wikipedia (3.4 times) and most major blogs. That’s already done. It’s not going backwards.
As of today - on post-ChatGPT Earth, I can talk to my phone and say:
“Just woke up. Here with wife, two kids, 3 & 5. Breakfast now. Kids don’t like snails. No tiny, tiny coffees. What are good things to do. Maybe a bike tour. Would need a child seat for one kid. Something on the river - boat trip. Double decker bus tours are good - if less than 90 minutes. Eiffel Tower at some point. Budget $300 per day.”
That simple AI interaction replaces 10 years of messing around with preferences in a fancy database. Nobody has built that today, but anybody could. The data is out there.
You could, on the other hand, pick apart that search and get a result using those sliders in the left column of an Experiences OTA. You could filter, sort, read loads of descriptions to hone in, check 14 relevant categories, look up availability on 10 products …You could get there. But it might take a few hours, and you might not end up viewing the best options.
With AI, you can run that actual voice search and get very specific results based on the entire request. You still need access to product information and a process for transactions, but I have a feeling Viator, GetYourGuide, TUI-Musement, etc. will be OK dealing with that part, in return for a slice of the commission. But Booking.com and Expedia aren’t getting a piece of it. It's impossible, without direct contracts.
So that’s the future in-destination travel assistant. You can safely assume that 200 startups are working on a solution like this right now. There are no barriers. This could be released by summer.
Booking.com and Expedia could also build this tomorrow. They won’t. They won’t move quickly enough. Airbnb ate their lunch 15 years ago while they were sleeping. With AI today, you can run 10 times, 20 times faster than 15 years ago. They don’t stand a chance.
So what we end up with is the Disconnected Trip. Which is probably fine. I’ll deal with my flight delays and hotel check-ins on my OTA app, and then I’ll switch over to my cool, fun, useful AI-powered travel assistant for all the good stuff.
Next time I travel I’ll remember the app that helped me 87 times during my last trip. By now, it’ll be an affiliate of Booking.com, Expedia, and it will have some Flight APIs plugged in, and so now this new app becomes … the Connected Trip. Everything, all in one place. Finally, success! IPO in 2025.
Of course, the big guys know this. Booking.com and Expedia are sitting on bags of cash and will swoop in at a time of their choosing. They’ll buy one of these AI startups, so in the end they’ll also, finally, end up with the Connected Trip.