Most travel dramas start with a delayed flight or a missing passport. But for one Spanish couple, the root of their holiday hiccup was something a little more digital. After showing up at the airport ready to jet off to Puerto Rico, they were denied boarding—because they hadn’t obtained the correct travel authorisation. The twist? They blamed the whole thing on ChatGPT.
A travel fail caught on camera
In a teary TikTok that quickly went viral, influencer Mery Caldass expressed her frustration, claiming the AI had misinformed her. “I asked, and it said no,” she sobbed on camera, referring to her question about needing a visa. “I don’t trust it anymore.” Her partner, filming the moment, seemed equally flustered as their travel plans came to an abrupt halt.
According to the couple, they had relied entirely on artificial intelligence to plan their trip, rather than consulting an embassy, airline, or an official travel site. And while ChatGPT had responded that no visa was needed for EU passport holders visiting Puerto Rico, what it didn’t spell out clearly enough (or they missed entirely) was that an ESTA authorisation—a required electronic travel document—was still mandatory.
The internet responds, and it's not all sympathy
Unsurprisingly, the backlash was swift. Social media users pointed out a key detail they had overlooked: Puerto Rico is a U.S. territory, meaning travelers from many countries still need a valid ESTA to enter. It costs approximately $21 and is usually approved within hours; however, not having it means you won’t be able to board that plane.
“ChatGPT was right, but you misunderstood,” commented one viewer. Others were more blunt: “Next time, check official government websites,” and “If you can’t take the initiative to verify this yourself, that’s on you.” The incident evolved into a cautionary tale about the overreliance on AI—and about asking the right questions in the first place.
So, is AI to blame—or user error?
Let’s be clear: AI tools like ChatGPT are potent for quick research, travel planning, and general advice. But they’re not foolproof. They work by providing generalised information, and they can only respond to what they're asked. So if you don’t ask the right question, you may not get the complete answer.
In this case, ChatGPT likely gave a technically correct reply—no visa is required for EU citizens visiting Puerto Rico—but it didn’t proactively mention the need for an ESTA. And that’s where things fell apart.
The real issue here isn’t that ChatGPT is unreliable—it’s about miscommunication and unrealistic expectations. It’s also a reminder that, while AI can help plan your trip, it’s still wise to double-check anything that could get you barred from boarding.
Happy ending in the end
Despite the bumpy start, the couple eventually made it to Puerto Rico and even caught a Bad Bunny concert in San Juan. Mery Caldass has since posted several sunny updates, confirming that all was forgiven—even if not forgotten.
So what’s the takeaway? AI is a handy co-pilot, but when it comes to visas, border control, and official rules, always double-check with the source that actually decides if you can get on the plane.
