Big Tech, Local Realities: Travel in the Age of AI
Booking.com’s Todd Lacey
Back in July I attended the Web in Travel (WIT) conference Queenstown edition. Hosted by its founder, Malaysian entrepreneur Yeoh Siew Hoon, the Singaporean-based travelling conference brought over 300 influential figures in travel and hospitality technology to the heart of the Southern Alps.
I’m like, not a super-techie person, and in my line of work as a travel and food writer, I don’t attend many conferences. So I felt a little like the odd one out in the room to start with, but my doubts melted away as I realised almost everything being discussed on the panels across the two days was relevant to what I do. I write about the end product in travel, and more importantly, about how the end product makes us feel – and how it connects us to a place and its people.
In the 20-something years since I first started travelling independently as a young backpacker with dog-eared Lonely Planet guide books and notebooks filled with friends-of-friends-with-spare-couches details (complete with Yahoo and Hotmail addresses) the extent to which technology has shaped the way we travel has changed can’t be exaggerated. And of course in very recent times the big question is how AI will shake things up even further.
I’m not doing a roundup from the conference themes here, but if I had took one key point away from the entire thing it would be that while AI is already playing a big role, we’ve a long way to go with trust, but what’s exciting is how far it might go with removing the friction points in both booking travel and doing the travel itself.
After the conference finished, I managed to pull up a chair with Todd Lacey, Oceania Regional Director for Booking.com. New Zealander Todd manages business growth, operations and strategy in Australia, New Zealand, the Pacific Islands and Korea. He’s now based in the Sydney office but spent some years in Seoul and has big love for the city – so watch this space for some insider tips on Seoul from Todd soon!
Todd’s passionate about diversity and inclusion in the travel sector. In 2021, he worked with the local team to lobby Booking.com’s global business to bring its world-class LGBTQIA+ accommodations training ‘Travel Proud’ to Australia and New Zealand.
Speaking to an online travel booking agency behemoth like Booking.com in little old New Zealand felt like fitting analogy for the industry – how do big tech platforms attempt to balance massive infrastructure with authentic, on-the-ground traveler realities? Over coffee at Kamana Lake House’s The Nest, we talked through the mechanics of trip planning, limits of AI, and which destinations Kiwis are hot for.
The Connected Trip
Anyone who travels regularly knows the administrative hassle of weaving a trip together. If you’re like me, you’re often juggling a number of apps to book flights, accommodation, and local transport, along with dozens of tabs on your browser to hunt down local food tours and dinner reservations.
Booking.com’s current strategic push centres on what they call the ‘Connected Trip’. "The travel experience today is very fragmented," Todd explains. "The connected trip is basically ‘how do we leverage all of the different technology that we have, and all of the different travel brands that sit under Booking.com and the infrastructure behind them, to create a much easier process for travellers?’"
In theory, The Connected Trip is like a self-curated package. Rather than locking travellers into a rigid traditional tour, users pick the individual pieces – flights, stays, cars, dining – and the platform links the boring backend stuff together.
Where tech platforms face their biggest test is when travel goes wrong. Todd is hopeful that if a flight is delayed or cancelled, connected systems would intervene automatically. "Ideally, we're able to solve that problem for you across the whole part of the trip before you even realise a problem has occurred," he says. "We've already got the solution, and we manage the whole process on your behalf."
Beyond the Discount
Loyalty schemes across the travel sector often feel a little dry; boiled down to a small room-rate discount you barely notice. Through their Genius program, Booking.com is trying to test whether non-monetary perks might be more enticing.
"One of the things we already test out in Queenstown is Genius Free Taxi," Todd says. "If you book over a certain value of accommodation, we may offer you a free taxi ride from the airport. And we're adding in different elements of Genius and value into other parts of the trip as well." The likes of flight seat selections and integrations with dining software like OpenTable open up more added value.
The AI Trust Deficit
There are more than 400 million reviews on Booking.com: that’s a lot of useful data that could inform future trips. The company is betting on natural language search models over traditional static filters to offer users options that best suit. Instead of checking off twenty boxes, you could type in a specific query, like finding a unique stay on the Amalfi Coast that doesn't require hauling suitcases up 200 steep stone steps (yes, that was our family… ouch). The AI will scrape actual guest reviews to flag such logistic details that could make or break your experience.
Algorithms are designed to track user behaviour over time. "If we know that you typically travel with family, or you typically stay at this type of property, then we'll start to curate and learn more about the customer over time," he says.
Yet, while Kiwis are quick to experiment with new tools, we remain cautious when it comes to handing over money. Booking.com’s own regional sentiment survey revealed that while interest in using AI for itinerary planning is high, only 3% of Kiwis currently trust an AI interface to execute a financial transaction.
"Even someone like me who uses AI a lot... I would be hesitant to put my credit card details in there today," he admits. "When you go through the travel experience at the moment on Gemini or ChatGPT and our interface pops up, we take you out of that and into the Booking.com experience where then we can securely process that transaction."
Where Kiwis Are Booking
Data presented at the conference revealed a clear divergence between Kiwi and Australian travel habits:
Australians are currently leaning heavily into domestic travel, with Sydney, Melbourne, and Cairns dominating search data. Kiwis maintain a significantly higher appetite for outbound international travel.
Vietnam and South Korea are seeing notable growth among Kiwi travellers despite ongoing direct flight limitations (I’m interested to see if Thai Airways returning to NZ will see an uptick in Thailand travel). For Kiwis, Japan and Bali remain the heavyweights for Asian outbound travel.
Domestically, Christchurch has seen a surge. As Todd notes, "Christchurch has the new stadium and sporting events, and increased flight capacity, so they've had positive things happening there."
As tech becomes more complex, the challenge for companies like Booking.com isn't so much about adding features, it’s about proving that algorithms can lessen the friction of a trip rather than add to it. Technology only delivers when it gets out of the way of the actual journey.
Pōwhiri to welcome delegates to WIT Queenstown
Japan remains one of the most popular Asian destinations for Kiwis
