These Tragic AI Fails Are Proof That You Can’t Fully Rely On ChatGPT To Plan Your Trip

As a travel writer who has visited over 100 countries, I recently decided to put AI planning tools to the test myself. For a 24-hour Alaska challenge I’m planning, I gave ChatGPT specific start and end times, plus non-negotiable requirements, including a helicopter ride in remote bear country, and dedicated rest time after the challenge before driving.

Despite my detailed parameters, it ignored the helicopter ride entirely and scheduled driving immediately after 24 hours with no sleep.

Even a simple weekend trip to Portland revealed serious flaws. The AI sent me across opposite sides of the city, suggested “short walks” to restaurants miles away, and had me arriving at attractions just before closing. It even scheduled my final activity to end at the same time my flight was departing, apparently believing I could teleport directly to my airplane seat.

What worries me most is when inexperienced families don’t spot these glaring mistakes before booking. Many are learning the hard way.

Such planning errors are common. Judy Gauthier, chief commercial officer of Go City, who has overseen the development of generative AI tools, discovered this while planning her family trip to the Smokies. “I used AI to recommend a waterfall hike that my family would love, and it repeatedly suggested the popular Laurel Falls Trail, which sounded perfect. Unfortunately, I later learned via a Smokies Facebook page that the trail was closed for an 18-month rehabilitation project.”

Gauthier also discovered how AI misinterprets context. When she asked about swimming in San Sebastián, Spain, AI warned her about shark dangers, apparently confusing the city’s aquarium with actual ocean conditions. “It turns out you could swim with sharks at the aquarium,” she explained, highlighting how AI pieces together fragmented information to reach inaccurate conclusions.

When families follow AI’s flawed recommendations, they risk vacation-ruining mistakes and often need help, as Parik Laxminarayan, co-founder of luxury travel company Enchanting Travels, has seen firsthand. He helped a guest on a Scandinavian holiday who used AI to book a hotel “only five miles” from dinner reservations, assuming taxis would be available. When no one serviced that remote suburb, the guest called in panic. The AI had calculated distance but ignored the reality of how to cover it.

These issues are more than anecdotal. Recent research found that OpenAI’s most advanced model achieves only a 10% success rate on complex travel planning benchmarks. Even with all the necessary information, AI failed to create viable plans 90% of the time.

Dr. Niusha Shafiabady, associate professor of computational intelligence at Australian Catholic University and director of the Women in AI for Social Good lab, explains why these tools struggle with travel planning. “Flight availability, prices, weather and traffic shift in real time, making it hard for AI to stay updated,” she said. “AI also relies on past data, but travelers make last-minute decisions that don’t always follow patterns.”

“Different airlines, hotels and transport systems have unique pricing models and formats that AI struggles to unify,” Shafiabady noted, adding that real-time adaptability remains a challenge.

“While AI is great for exploring ideas, using it for actual travel planning is a gamble,” said Nolan Burris, a training consultant with Signature Travel Network. “It often ignores how seasons or local holidays impact what is possible. AI hallucination is a big problem, from inventing sites that don’t exist to conflating mismatched details from real ones.”

Beyond technical glitches, AI also misses something more fundamental about travel planning. AI-generated itineraries often default to the most popular or highly reviewed experiences, but what’s “top-rated” isn’t always right for honeymooners seeking privacy or multigenerational families needing logistical simplicity. “Travel is so personal, and AI falls short in crafting a journey that is built around the individual,” explained Chris Brunning, co-founder of Untold Story Travel. “While it can feed you a list of the top sites, plot your transportation options, and suggest hotels, it lacks the human connection that makes travel so special.”

These failures explain why my Alaska plan fell apart so badly. AI tools miss what experienced travelers know instinctively, like factoring in airport arrival times, avoiding geographically incompatible activities, and allowing time for rest. It gets even trickier for first-time visitors, who often don’t know to check for seasonal closures, transportation gaps, or whether those “quick” distances are actually realistic.

Despite slick interfaces, the technology isn’t ready for the complexity of real-world travel logistics. As Shafiabady puts it, “AI provides guidance, not certainty. It suggests optimal plans but can’t predict every disruption.”

Her advice for travelers considering AI tools: “Always double-check AI-generated itineraries, especially for multi-stop trips. Unexpected changes may require manual adjustments, and AI depends on available information, which might not account for last-minute travel disruptions.”

If you use AI for brainstorming, treat every suggestion as a rough draft needing fact-checking. Verify hours, seasonal availability, and distances using official websites, as well as TikTok, Reddit and destination-specific Facebook groups where travelers share real-time updates on what’s open or closed, or worth skipping. Build in buffer time and remember that realistic travel takes time. It’s best to think of AI tools as research assistants, not travel agents.

Until AI accounts for the basic laws of physics and human biology, use these tools for inspiration only.

Or wait until you can actually teleport to your airplane seat.