A traveler lands in a foreign country, stepping off the jet bridge and immediately reaching for their smartphone. This singular, instinctive action has become the modern ritual of arrival. In the digital age, the device is no longer just a communication tool; it is the master key to the journey. Boarding passes, hotel reservation details, ride-hailing credentials, interactive maps, secure payment platforms, and urgent messages all reside within a single screen. Every one of these services operates under a fundamental, often unspoken assumption: that a reliable, high-speed data connection is waiting on the other side of the border.
When that connection falters, the friction is immediate and often paralyzing. A hotel may lose contact with a guest expected to arrive at midnight; a ride-hailing application may fail to bridge the gap between a driver and a passenger in a crowded terminal; an airline’s digital concierge may go dark at the exact moment a flight is canceled.
This pervasive vulnerability in the modern travel ecosystem was the focal point of a critical discussion between Richard Trinder, senior director of strategic partnerships at travel eSIM provider Holafly, and Dan Marcec, intelligence editor at Skift, during the Skift Global Forum 2026. As the industry grapples with increasingly complex traveler expectations, the consensus is clear: no single entity controls the end-to-end journey, yet a connectivity failure is universally blamed on the brands involved. For leaders like Trinder, mitigating this risk requires a shift in philosophy, moving connectivity from an optional add-on to a foundational element of the travel experience.
The Trip Begins With a Connection
“The smartphone has increasingly become the control center of our lives,” Trinder noted during the forum. This transition is not merely a convenience—it is a transformation of the traveler’s infrastructure. When the smartphone cannot connect, the traveler is essentially stranded in a digital vacuum. With boarding passes and identity documents tethered to a digital interface, losing connectivity is no longer just an inconvenience; it is a full-blown crisis.
This dependence on digital infrastructure has irrevocably altered consumer behavior. For decades, the travel industry has conditioned consumers to expect seamless, on-demand experiences. From one-click bookings to instant notifications, the bar for efficiency has been set high. Consequently, travelers now demand that this same reliability persists as they move across borders, switch between international networks, and navigate disparate service providers.
The points of transition—international border crossings and bustling airport environments—remain the most vulnerable touchpoints. As travelers cross connectivity zones, service interruptions are common. Furthermore, reliance on public airport Wi-Fi introduces risks related to stability, security, and potential cyber threats. The consequences of these failures are magnified when travelers are in a state of flux, needing to retrieve crucial information or reach out for assistance during a delay or disruption.
Marcec highlighted a significant paradox in the current travel landscape: a hotel, for instance, has no control over the connectivity infrastructure of a remote airport. Yet, when a guest cannot access their digital reservation or communicate their arrival time due to a network failure, the guest’s frustration is directed squarely at the hotel brand. Trinder warned that these micro-breakdowns in connectivity have long-term consequences for customer satisfaction, brand loyalty, and, ultimately, the likelihood of repeat business. In an era where the traveler has zero tolerance for friction, a failure to stay connected is, in effect, a failure of the brand promise.
Peace of Mind Without Thinking About Data
During their conversation, Marcec likened the role of connectivity to basic hotel utilities like clean water and air conditioning. These are services that travelers expect to function perfectly in the background, only noticing them when they fail. Trinder agreed, framing connectivity as an essential modern utility. “It’s just like the air we breathe and the water we drink,” he observed.
At Holafly, this perspective dictates a company-wide focus on "peace of mind." The objective is to provide travelers with a sense of security by proactively anticipating connectivity hurdles before they escalate. The stakes are often more than just a matter of convenience; they are deeply personal. A business traveler racing against a critical project deadline or a family member needing to send an urgent, time-sensitive message faces a high-pressure scenario. In such instances, the inability to connect transforms a manageable travel challenge into a significant, often distressing event.
Trinder argued that the industry must pivot toward preemptive solutions. Rather than placing the burden of solving connectivity problems on the traveler—who is already navigating the stresses of transit—travel companies should integrate these solutions into the customer journey from the beginning. While connectivity services represent a relatively small portion of the total travel spend, their impact on the overall customer experience is disproportionately large. When everything is functioning, the technology remains invisible; when it breaks, it becomes the only thing the customer notices.
A Journey No Company Owns Alone
Delivering this level of reliability requires an unprecedented level of coordination across a fragmented industry. Airlines, hotels, booking aggregators, and connectivity providers each manage different segments of the travel lifecycle, yet the traveler expects a singular, frictionless experience.
Marcec connected this challenge to a broader trend observed throughout the Skift Global Forum: major travel players, including giants like Uber and Airbnb, are striving to exert greater control over the end-to-end journey. However, even as these firms expand their operational scope, they remain inherently reliant on external services. “No one travel provider or travel company in this room owns the journey end-to-end completely,” Trinder remarked. “We have to partner up.”
For Holafly, the path forward involves a fundamental shift in how connectivity is delivered. Trinder advocates for moving away from the traditional model, where an eSIM is treated as a secondary, standalone purchase. Instead, he envisions a future where travel brands embed connectivity directly into their native booking flows and digital service ecosystems.
Through the use of application programming interfaces (APIs) and software development kits (SDKs), connectivity can be woven into a partner’s existing application interface. This integration ensures that the tool is available at the exact moment of need. The business case is compelling: travel brands have invested heavily in their apps and digital platforms to drive engagement, yet they fail to capture the full value of those investments when the user loses their connection.
Trinder pointed to the maritime and cruise industry as an ideal candidate for this integrated approach. Passengers at sea frequently face the challenge of moving through varying connectivity zones or experiencing total blackouts. By leveraging Holafly’s global coverage—spanning over 200 destinations—travel providers can mitigate these interruptions. However, Trinder emphasized that technical integration is only half the battle. Success, he noted, relies on joint business plans where companies agree on shared objectives and responsibilities. By aligning on measures like ancillary revenue and customer experience metrics, partners can ensure that connectivity remains a priority.
Furthermore, he stressed the importance of human intelligence in an increasingly automated world. “We need humans to talk to each other in companies,” Trinder stated. While the back-end complexity is handled by code, the strategy requires teams to collaborate across organizational lines to ensure that the traveler is shielded from the friction of the underlying technology.
Always On as a Safety Net
The importance of this “always-on” capability becomes most apparent when travel plans unravel. Whether it is a missed connection, an unplanned layover, or a sudden change in plans due to external factors, the moments that require the most information are often the moments when connectivity is most at risk.
Trinder cited Holafly’s “Always On” initiative as a prime example of a solution designed for these disruptions. By providing a foundational layer of data that remains available for essential tasks, the service acts as a safety net. This ensures that even if a traveler experiences a service glitch, they retain the ability to handle critical communications and access vital information. The goal is to eliminate the need for the traveler to navigate the logistics of purchasing a new data plan in the middle of an emergency. “Always On will give you that peace of mind that you’re okay,” Trinder said. “You can do the emergency things you need to do.”
What Comes Next
As the travel industry accelerates its adoption of AI-powered services and agentic AI, the need for robust connectivity becomes even more acute. Marcec noted that as companies invest in sophisticated digital customer service tools, these innovations remain entirely dependent on the traveler being connected. Without reliable access, even the most advanced AI concierge remains inaccessible.
Trinder believes that the time for companies to prepare is now. By integrating connectivity into existing purchasing flows and technical frameworks today, brands are effectively "laying the plumbing" that will allow them to adapt to future technological shifts. He predicted that within the next two years, eSIM connectivity will be viewed as a routine, standard utility, much like contactless payments or digital boarding passes are today.
Looking ahead, Holafly aims to evolve from a connectivity provider into a true travel companion. The vision includes building additional services atop this connectivity foundation to provide travelers with the right information at the right time. Ultimately, the industry’s trajectory is clear: the technology will continue to become more sophisticated, but the goal remains remarkably simple. As Trinder summarized the core mission for travel brands: “How do we make it easy and peaceful for you?”
