Published on August 20, 2025
Planning a trip? Remember that having the right paperwork is a must. Lately, many of the travellers are using smart tools like ChatGPT to get quick travel tips. But a recent story shows that leaning on AI without double-checking can cost you.

A Travel Mishap in Puerto Rico: The Case of the Missing Visa

A content creator from Spain recently found herself stranded at an airport in New York after receiving inaccurate travel advice from an AI assistant. The creator who was planning a trip with her boyfriend to Puerto Rico to attend a Bad Bunny concert, turned to ChatGPT for visa information. According to the AI, no visa was required for her to travel to the United States, which was true as European citizens generally do not need a visa for tourism stays under 90 days. However, what the AI failed to mention was that she would still need approval through the Electronic System for Travel Authorization (ESTA) before boarding the flight.

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Without the necessary ESTA approval, the couple was denied boarding at the airport, leaving them unable to reach their destination. This unfortunate event is a stark reminder to travellers that AI tools, though helpful, cannot replace the accuracy and reliability of official government sources.

Why AI Isn’t Always the Best Travel Adviser

While AI tools like ChatGPT can offer guidance on a wide range of topics, they are far from foolproof when it comes to travel-related questions. Inaccurate or incomplete information could lead to mistakes like the one Caldass experienced, resulting in missed flights, last-minute scrambling for documents, and stress. AI might provide general advice, but for anything related to visas, travel authorisations, or entry requirements, turning to government websites and official resources is essential.

For example, the United States Department of Homeland Security (DHS) provides clear guidelines on visa and ESTA requirements for citizens of countries participating in the Visa Waiver Program. While AI might give general advice on the need for a visa, the full details, including the ESTA requirement, are only available from trusted government portals. Likewise, other countries, such as Puerto Rico, which is a U.S. territory, have specific travel regulations that require checking local immigration websites.

The Importance of Double-Checking AI Travel Advice

Given that AI tools draw on vast amounts of data to provide answers, there’s always a chance that the information it delivers may not be fully up to date or entirely accurate for every traveller’s situation. For instance, visa requirements can change depending on current government policies or international relations. What was true yesterday might not be true today.
For travellers heading to destinations like Puerto Rico, San Juan, or the U.S., it’s always safer to visit official government websites for the most accurate and current travel advice. The U.S. Department of State and the Electronic System for Travel Authorization (ESTA) page are the definitive sources of information regarding U.S. entry requirements. They provide details on visa types, ESTA applications, and other essential travel documentation.

How to Avoid AI-Related Travel Mistakes

To ensure smooth travels and avoid potentially disastrous situations, here are some simple steps for travellers when planning trips:

1. Use Government Websites: For visa, entry, and immigration information, always check the relevant official government website of the country you are visiting. Websites such as gov.uk, us.visas.state.gov, or the ESTA website provide official, up-to-date guidelines.
2. Double-Check Travel Authorisation: Even if you’re told you don’t need a visa, make sure you check the Electronic System for Travel Authorization (ESTA) for countries in the Visa Waiver Program, such as the U.S., before your departure.
3. Book with Flexibility: If you’re not entirely sure about entry requirements, it’s better to book travel that allows flexibility in case last-minute changes or document issues arise.
4. Use AI as a Supplementary Tool: AI is excellent for general travel tips, like finding the best local restaurants, landmarks, and events, but should not be relied upon for vital legal and immigration-related information.

A Growing Trend: More AI Travel Mistakes

While this case is not unique, it highlights a growing trend of people turning to AI tools for travel planning. As AI becomes more integrated into daily life, there will likely be more situations where individuals mistakenly rely on these systems for critical travel advice. However, while AI continues to improve, it still cannot replace the authority and accuracy of government websites for matters of legal documentation and travel compliance.
For anyone planning to visit high-profile destinations such as San Juan, Palo Alto, Los Angeles, or any other U.S. city, relying solely on AI advice for visa or ESTA requirements can lead to serious consequences, including missing out on a once-in-a-lifetime concert or trip.

Stay Ahead of Travel Surprises by Double-Checking Your Documentation

In today’s busy travel world, using AI and smart tools feels tempting, right? But, for key steps like checking visa rules, ESTA approvals, and entry rules, trust official government sites, relying totally on it can be costly. Whether you’re headed for Puerto Rico, the shimmering San Francisco Bay, or anywhere else, double-check the travel papers you need. Do this ahead of time, and you’ll glide through the airport, confident and calm. Cross that line off your travel to-do list and skip the last-minute panic that might keep you from boarding at the gate. Staying informed keeps your trip fun and flying smooth.

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Tags: puerto rico, redwood city, San Francisco, U.S.

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