Skift Take

From the wishful thinking and hype of years ago, the connected trip is beginning to draw real investment and become a thing. It will take a very extended period of time to make it a more meaningful development. In that faraway horizon, will there indeed be any differentiation among the leading providers?

High-stake online travel agency competition used to merely revolve around how many tens of thousands of hotels, or homes and apartments each company added to its ranks during the previous quarter, and those milestones are still very much in play.

But lately a new and somewhat more esoteric flashpoint has emerged, namely the connected trip. Enter Booking Holdings and Expedia into this fray.

Travel industry executives have referred to the concept by various names, including the connected trip, the perfect trip, even frictionless travel, and the idea has been bandied about for years.

Five years ago, then-Concur CEO Steve Singh dreamed of the perfect trip, where an app would float flight-rebooking recommendations when a flight was delayed, the hotel check-in process could begin when exiting the plane, and further down the jetway a car rental option appears on your phone. The company even had the Perfect Trip Fund to nurture startups to help in the mission.

But with advances in mobile, artificial intelligence, and a consequent stampede toward personalized services for travelers, the connected trip is attracting real investment and is gaining momentum.  As Lorraine Sileo, Phocuswright’s senior vice president of research, put it Wednesday at the company’s conference in Hollywood Beach, Florida, “The connected trip is what we are all striving for.”

However, in these early moments of the trend, it’s still unclear to what degree the buzz will turn into tangible bottom line benefits.

Glenn Fogel, CEO of Booking Holdings, doesn’t need an invitation to expound on the topic, which he has been promoting for a couple of years. On the sidelines of the conference, Fogel told Skift it makes sense that Expedia is now talking about the connected trip, as are Airbnb, TripAdvisor,, and others.

Fogel said, though, that his company has an advantage in that it has “more capital” to devote to the connected trip than others in travel, more demand, data, and he assumes more technologists working on it.

“I’m feeling good where we stand in terms of our progress, and I’m looking forward to further advances as we evolve,” Fogel said.

As a public company, one of the few concrete measures of the company’s advances toward the connected trip that Fogel is willing to point to is the company’s growth in rental car days, which climbed 8.5 percent to 21 million in the third quarter, the largest jump by far in at least two years. Fogel attributes this to the company’s experimentation in offering the right car type — a van or “people-mover” for a group’s hotel booking, for example — to the appropriate customers.

Fogel said mobile apps will be at the center of the connected trip, and artificial intelligence will help determine if the company offers a free or greatly reduced airport transfer for a usually high-spending or loyal customer, for example. The company struck a deal to offer premium seating in hard to book restaurants in a partnership between its OpenTable unit and CapitalOne. entrance lanes at popular attractions are already realities, and airport lounge access for Booking Holdings customers is another possibility.

He likes Booking Holdings advantages over Expedia in moving toward the connected trip, citing a much larger and more global accommodations business, for instance.

“The biggest advantage in anything in technology is scale,” Fogel said.

When asked at an investment conference Tuesday whether Expedia Group actually has the advantage because Expedia has long been a full-service travel company, Fogel said Expedia has mostly done cross-selling, and seemingly isn’t far along when it comes to the connected trip.

Expedia Is Talking the Talk

But, Expedia, too, and more recently than Booking Holdings, is touting the connecting trip.

In response to an analyst’s question about holistic travel during the company’s third quarter earnings call November 6, Expedia Group CEO Mark Okerstrom said: “So the team’s got a bunch of plans to actually build more in the way of the connected trip’s experience beyond what is our traditional core competitive advantage, which is being able to bundle things together, have your itinerary all in one place and do so in a way that ultimately can deliver great savings for our customers.”, for example, intends to enable users of its app to import a flight booking made on, and to put it into an itinerary when it includes an Expedia hotel booking. If the United flight gets delayed, then Expedia will notify the hotel on behalf of its customer.

In another manifestation of the connected trip, at selected hotels Expedia is already enabling some loyalty program members to select a perk, such as a fruit bowl, to have waiting for them at the hotel when they arrive late at night, for example.

Expedia might argue, too, that a companywide reorganization over the last several months, which combined tech teams that were previously separated into units according to the particular brand they worked for, will accelerate the drive toward the connected trip.

Technologists at Expedia Group’s homesharing unit Vrbo, for instance, plan to share and help develop tools for the company’s Expedia Local Expert tours and activities business to improve the customer experience.

At both Booking Holdings and Expedia Group, each company’s assorted brands — and at Booking, and Vrbo and Expedia Local Expert at Expedia Group, for example — are attempting to collaborate more closely.

It’s all designed to take the hurt out of the frazzled traveler, and to engender a smoother trip.

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Tags: airlines, booking, booking holdings, cars, connected trip, expedia, flights, hotels, trip planning

Photo credit: Travelers check an information monitor as weather causes flight cancellations and delays during a winter storm in Boston, Massachusetts, February 5, 2014. 132656 / 132656

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