Travel Influencer Asked ChatGPT If She Needed A Visa — Then Her Puerto Rico Trip Collapsed

Last week Spanish social media influencer Mery Caldass uploaded a video from an airport, crying as she shared that her travel plans to Puerto Rico had fallen apart: “I asked ChatGPT if I needed a visa, and it told me no.” She says her dream trip collapsed because she relied on ChatGPT.

“That’s what I get for not double-checking.” And she said “I don’t trust that one anymore,” she was done relying on AI assistants for important travel decisions. She mused that this all was some sort of AI ‘revenge’ because she’s often insulted ChatGPT in her chats.

@merycaldass

si hay una revolución de las IAs voy a ser la primera 4niquil-hada‍♀️

♬ sonido original – Mery Caldass

Her travel wasn’t too disrupted since she posted video from the Bad Bunny concert in Puerto Rico the following day. She’d have applied for the ESTA, gotten it approved, and flown.

@merycaldass

this is how it is to travel to Puelto Rico papii to see the rabbit malo ☺

♬ sonido original – Mery Caldass

Caldass, who has about 400,000 followers on Instagram travels around and posts photos and videos of herself prancing around her destnations. She calls herself a Comedian. Her TikTok has nearly a million followers and over 42 million likes. This is her pinned Instagram post:

Pro-tip: This Star Alliance web page does a nice job letting you see the entry requirements for each country based on your passport and where you’re entering from.e

However, I asked ChatGPT the visa the question and was told,

Spanish citizens don’t need a visa to travel to San Juan, Puerto Rico—but you do need an ESTA under the U.S. Visa Waiver Program.

I didn’t even do anything complicated here. I let GPT-5 use its own router to decide the model it would use, and it answered immediately (no ‘Thinking’ or ‘Pro’). I then forced it to answer with 4o and was still told, “No, a Spanish citizen doesn’t need a visa to travel to San Juan (Puerto Rico), but you do need a valid ESTA.”

If she asked in Spanish — “¿Necesito una visa para ir a Puerto Rico siendo ciudadana española?” — the model may have mapped “visa” narrowly. In everyday Spanish usage, “visa” may be understood as “formal visa requirement,” not an ESTA-like preclearance. That could bias the model toward a simple “no” thinking that’s what the user wanted. She also might have asked “Do I need a visa? Just answer yes or no.”

Spanish prompting is likely to produce less context.

  • U.S. government sources are in English
  • Written answers in Spanish the model would have trained on are less likely to mention the ESTA because it’s assumed-knowledge. (Everyone knows you can’t just come to the United States.)
  • So trining model bias is going to lead to incomplete answers in Spanish.
  • Plus, translation issues – with visa being treated more formally in Spanish.
  • And the English ChatGPT is more tuned to ‘safe detaults’ like giving disclaimers (in this case, about ESTA)

How you prompt matters, but less so than it used it. The model you use matters, but less so than it used to. AIs hallucinate, but a lot less than they used to. In fact I’ve yet to be able to make the ‘thinking’ versions of GPT-5 do so.

And the answer this influencer got wasn’t even wrong, they did not require a ‘visa’ at least the U.S. doesn’t call an ESTA a Visa – it’s the advance registration requirement for travelers from Visa Waiver countries. I still think of it as a Visa, and if you’re asking about a visa you’re probably thinking of ‘what are the things I need to do in advance to travel’.

You need Electronic Travel Authorization to fly to Australia and now the U.K., and soon an European Travel Information and Authorization System (ESTA) for (non-Europeans to travel to) Europe. Travel is increasingly being encumbered.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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Comments

  1. What an idiot.

    I would never use the non-official website for this question (either my country’s listing of required documents or the destination country’s border controls).

  2. Who’s the bigger idiot… the influencer idiot, or the idiots who are influenced by her?

  3. Every time I travel abroad, I get automated reminders from the airline about visas and stuff that I might need. All airlines, foreign and domestic, want your passport information before flying internationally, usually at the time of booking. Maybe non-US airlines don’t send visa reminders/info… God knows their websites and apps mostly suck. But still.

  4. I am teaching online college geography classes and increasingly see students use AI for their essays. It is easy to tell when they do, the facts are either slightly out of date, occasionally dead wrong or so generalized as to be useless. (Conversely you really can tell when people are paying attention, do their own research and think for themselves.) Unfortunately taking the easy way out, using tools that dumb things down, and not checking your answers seems to be becoming more common. The results are obvious, in travel and many other activities.

  5. Oh, I know just how the “influencer” feels about Chat whatever being wrong about that visa.

    I learned the hard way when I lost my shirt after relying on “Imakethebigbucks182” for financial advice once.

    What’s this world coming to when you can trust the veracity of the internet?

  6. I use Wikipedia’s “Visa requirements for United States citizens” and haven’t had an issue yet.

  7. The horror of relying on AI or your cousin for information. F around and Find Out. Influencers are gross. Asking random people to support your life so you can be lazy AF? It’s genius and deplorable at the same time

  8. Considering that eyeballs are everything to an influencer, even a post of them crying in their misery is eyeballs. You spread it, you fell for it.

    Having said that, all the electronic per-authorization is not encumbrance. It’s a pre-vetting process that makes port of entry go faster. You want to stand in line for an hour the old school way? Or would you like to be eligible to walk up to the automated passport control kiosk and get through in five minutes?

    It’s all good, except for the fees. Japan will be joining soon too.

  9. Huh… so it turns out Puerto Rico is part of the USA after all…

    For those of us who actually travel, we should be in-favor of the free movement of people, less encumbrances, especially for tourism which supports the destination economy.

    And, Gary, most importantly, thank you for including photos. It helps us to do our own ‘research’ on these topics. More like, Cal-d(at)-ass.

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