Booking Holdings’ ‘connected trip’ vision never materialized, and AI is the latest threat
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%
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