The first time Booking Holdings CEO Glenn Fogel coined the term “connected trip” as a formal corporate strategy in public was during the company's second-quarter earnings call in 2019.
Fogel laid out the vision as follows: “Our long-term vision is what we call the connected trip ... It is about building a seamless, holistic system that gives and does everything for the traveler, makes their lives easier and gives value to them.”
Seven years in, the “connected trip” has outlasted even generative artificial intelligence (AI) as a quarterly earnings buzzword. A beautiful corporate vision in investor decks and completely nonexistent in reality.
Booking.com has in the meantime successfully diversified from its core accommodation; their standalone flight volumes now compete head-to-head against the leading flight online travel agencies (OTAs) in scale, and their cross-selling engine from accommodation bookings to transfers, rental cars and activities is firing on all cylinders.
But behind the scenes, these services still live in completely separate universes. The moment your journey hits a snag, you realize there is no omniscient customer support team ready to patch your itinerary back together.
The industry's most popular travel combo, flight + hotel, which was pioneered by Expedia back in internet prehistory in 2001, remains in Booking.com a basic Lastminute.com white label that lives outside the travel giant's massive account and loyalty ecosystem.
Why has the grand vision of seamless travel been indefinitely delayed? It comes mostly down to three major technical and legal roadblocks.
The outsources flight ‘glue’
For a platform built on accommodations, flights are the natural “glue” that starts a travel itinerary and dictates the timing of hotels, cars and activities. However, Booking.com historically outsourced the majority of its flight fulfillment to Etraveli under its Gotogate brand.
Booking Holdings attempted to acquire Etraveli to gain full operational control, but that plan collapsed in 2023 due to intense European Union antitrust concerns, leaving the critical flight layer disconnected from the accommodation and rest of travel services.
The outcome? If you look closely today at the fine print of a flight booked through Booking.com, you usually land in Gotogate’s cobranded terms and conditions, where chapter seven, “Special Provisions for the Mediation of Bookings of Multiple Services” describes in typical legal jargon the very opposite of what the connected trip vision should stand for, essentially stating, “We will happily let you mix and match your own connected trip, but the second a flight gets canceled, we legally transform into an innocent bystander.”
The merchant payment quest
To actually pull off the connected trip, Booking had to rebuild its financial plumbing. Under its successful agency model, the travel giant just passed your card details to the hotel to handle; but to connect multiple travel services into one single journey, it had to pivot to a “merchant” model where it takes the cash directly for the full transaction.
According to U.S. Securities and Exchange Commission filings, this payment infrastructure overhaul successfully flipped the Booking Holdings' business from a 27% merchant mix in 2019 to a dominant 70% in recent quarters, meaning the financial rails are finally mature enough to support its grand travel vision.
The liability minefield of tour operating
The perhaps most significant reason for delaying connecting multiple services under one transactional umbrella is the tour operator liabilities that come with it.
While OTAs shield themselves from cross-vertical operational failures in standalone travel services, legal frameworks like the EU Package Travel Directive forces operators bundling travel services to completely absorb the financial and operational fallout of chain-reaction risks, including alternative arrangements and mandatory care and accommodation duties.
For an online marketplace like Booking.com built on light assets and high margins, absorbing the real-world fallout of global travel delays and cancellations across millions of itineraries represents a ticking bomb in its balance sheet.
The agentic coup: Shape up or get swapped
During a recent investor interview, Fogel reiterated the long-held corporate dream, using a vivid analogy: “Unfortunately, travel is like dominoes—when one thing falls apart, a bunch of other ones fall apart on top of it … That is what we're building. It takes time. Rome wasn't built in a day, and neither will our connected trip.”
While seven years is admittedly stretching the definition of “a day” to its breaking point, Booking Holdings is running out of runway to finally get its act together before the AI wave flushes them and their vision into irrelevance.
The rise of agentic AI presents an existential threat. General-purpose agents and conversational search engines are positioning themselves not only as the new front doors for travel discovery but as personal AI assistants that will organize and manage customers' end-to-end travel journeys.
If Booking.com remains a fragmented collection of standalone travel services, there is a real risk of being degraded to a commoditized fulfilment provider of loose segments in the overall trip, hidden away behind a primary AI interface.
The connected trip is the travel tech incumbent’s best bet to hedge the risk against disintermediation. By blending accommodation, flights and other services into one living, interconnected itinerary tied to your personal Genius account, consumers will be motivated to instruct their AI assistant to book the entire trip within the OTA’s ecosystem.
Booking.com spent years building the financial plumbing and scaling its vertical offerings but kept the connected trip vision safely contained within the fictional universe of investor relations.
Now, the travel giant faces a stark existential choice: It must either bite the bullet and absorb the financial liabilities that come with guaranteeing true travel protection when a trip falls apart or watch from the sidelines as the agentic revolution executes its vision for them.
If AI agents take over the messy, real-time orchestration of end-to-end travel, Booking risks seeing its years-long investor dream built, owned and run by someone else's algorithms.
About the author...
Mario Gavira is CMO of
Travelier, as well as an angel investor.