Booking Holdings is coming at AI with five main initiatives, including two internal startups and a soon-to-be-launched Agoda trip-planning tool. Expedia dropped its all-encompassing chatbot Romie and is now building specialized AI agents that communicate with one another. For corporate allocators at travel companies sizing AI investment, the Booking/Expedia divergence is a live natural experiment.

Booking and Expedia are betting on opposite AI futures. In seven days, both take the SGF stage to make their case.

Plus a capital-allocation session on where travel money should move next, and the CEOs of Airbnb, Hilton, and Accor on the decisions their sectors face.
56 tickets remain.

Time Horizon: 6–18 months

Should a travel company fund several independent AI experiments at once, or consolidate around one connected multi-agent system?

OTA product chiefs — placing multiple AI bets at once · Corporate finance allocators — sizing 2027 AI capex · Travel-tech deal advisors — pricing the next AI acquisition

Booking Holdings is spreading five AI bets across its brands and two outside startups. Expedia killed its all-in-one chatbot and rebuilt around a single connected agent network.

Demand — India's Domestic Tourism Boom May Be Its Biggest Inbound Problem — Peden Doma Bhutia

Operations — Wyndham's Newest Brand Is a Boutique Spin-Off of Dolce Hotels — Luke Martin

Policy — Thailand Tightens Entry Rules to Focus on 'Quality Tourism' — Montira Rungjirajittranon

Priceline's Penny engagement data: whether conversion gains hold as the sample grows past earnings-call anecdotes.

Agoda's trip-planner launch: how closely it mirrors Penny's top-of-funnel approach versus Booking.com's bottom-up build.

Expedia's multi-agent rollout: whether the specialized-agent architecture shows measurable booking lift within two quarters.

Online travel agency usage falls off sharply with age, from 57% of 18-24 flight bookers down to 25% of travelers 65 and older, according to Skift Research.

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Waiting for certainty could mean falling behind. A new report outlines five moves to protect revenue and margins while continuing to invest.

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Pay per booked night. No pay per click. Minimum bid of $5. Vrbo's new sponsored listings are live, and in this clip from Good Morning Hospitality, A Skift Podcast, Tim Rosolio, Vice President of Vacation Rental Partnerships at Expedia Group, breaks down exactly how the auction works, why this is the visibility solution hosts have been asking for, and why Vrbo is not going to let bad partners drag down conversion just because they outbid everyone else.

How are public travel companies performing around the world? The Skift Travel 200 pulls the data you need to understand global market movements. Paid subscribers get full access here.

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